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Chemical Structure| 1142197-14-5 Chemical Structure| 1142197-14-5

Structure of 1142197-14-5

Chemical Structure| 1142197-14-5

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Product Details of [ 1142197-14-5 ]

CAS No. :1142197-14-5
Formula : C8H8BrN
M.W : 198.06
SMILES Code : BrC1=NC=C(C2CC2)C=C1
MDL No. :MFCD11869551
InChI Key :WCHBRVOAPMMHIR-UHFFFAOYSA-N
Pubchem ID :45788476

Safety of [ 1142197-14-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 1142197-14-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 6
Fraction Csp3 0.38
Num. rotatable bonds 1
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 44.4
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

12.89 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.25
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

2.79
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

2.66
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

2.22
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

3.12
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.61

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.2
Solubility 0.124 mg/ml ; 0.000626 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-2.72
Solubility 0.38 mg/ml ; 0.00192 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-3.48
Solubility 0.0656 mg/ml ; 0.000331 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.53 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

2.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.91

Application In Synthesis of [ 1142197-14-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1142197-14-5 ]

[ 1142197-14-5 ] Synthesis Path-Downstream   1~34

  • 1
  • [ 1169563-99-8 ]
  • [ 1142197-14-5 ]
  • tert-butyl 4-(5-amino-1-(5-cyclopropylpyridin-2-yl)-1H-pyrazol-3-yl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate;copper(l) iodide; (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane; In dimethyl sulfoxide; at 130.0℃; for 15h;Inert atmosphere; sealed tube; A mixture of tert-butyl 4-(5-amino-lH-pyrazol-3-yl)piperidine-l-carboxylate (300 mg, 1.126 ramol), <strong>[1142197-14-5]2-bromo-5-cyclopropylpyridine</strong> (234mg, 1.183mmol), copper(I) iodide (21.45mg, 0.1 13mmol), (lS,2S)-NN2-dime ylcyclohexane-l,2-diamine (16.02 mg, 0.113 mmol), and cesium carbonate (734mg, 2.253 mmol), DMSO (3 rnL), was purged with N2 for 30 min. The mixture was heated to 130 C in a sealed tube for 15 h. The mixture was cooled to rt. and water (30 mL) was added. The mixture was extracted with EtOAc (3 x 30 mL). The combined organic extracts were dried (MgS04) and concentrated in vacuo. The residue was purified by silica gel chromatography, eiuting with a solvent gradient of 0 to 40 % EtOAc in hexanes to give the product as a white solid. 1H NMR (400 MHz, CDC13) delta 8.03 (m, 1H), 7.74 (m, 1H), 7.32 (m, 1H), 5.88 (bs, 2H), 5.26 (s, 1H), 4.10 (m, 2H), 2.79 (m, 2H), 2.67 (m, 1H), 1.88-1.79 (ra, 3H), 1.61-1.54 (m, 2H), 1.42 (s, 9H), 1.20(t, J- 7.2 Hz, 1H), 0.94 (m, 2H), 0.63 (m, 2H).
  • 2
  • [ 1142197-14-5 ]
  • (5-cyclopropylpyridin-2-yl)acetic acid [ No CAS ]
  • 3
  • [ 1142197-14-5 ]
  • [ 1334783-12-8 ]
  • 4
  • [ 1116-98-9 ]
  • [ 1142197-14-5 ]
  • tert-butyl cyano(5-methoxypyridin-2-yl)acetate [ No CAS ]
  • 5
  • [ 1142197-14-5 ]
  • 2-bromo-5-cyclopropyl-1-(λ1-oxidanyl)-1λ4-pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
98.6% With 3-chloro-benzenecarboperoxoic acid; In chloroform; at 20.0℃; Step 1 : <strong>[1142197-14-5]2-bromo-5-cyclopropylpyridine</strong> -oxide (245) [0747] To a solution of <strong>[1142197-14-5]2-bromo-5-cyclopropylpyridine</strong> (2.0 g, 10.1 mmol) in CHCI3 (10 mL) was added m-CPBA (2.62 g, 15.2 mmol). The reaction was stirred at room, temperature overnight. The mixture was diluted DCM and washed with 5% aq. NaHCC solution and brine. The organic layer was dried over anhydrous NaiSCH, filtered and concentrated. The residue was purified by column chromatography on silica gel eiuted with PE/EtOAc (30: 1 to 1 : 1) to give compound 245 (2.12 g, 98.6 % yield) as a white solid. LC/MS (ESI) m/z: 214 (M+H)+
With 3-chloro-benzenecarboperoxoic acid; In chloroform; at 50.0℃; for 4h; To a stirred solution of (2S,4R)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid (125 mg, 0.54 mmole) in 8 mL of CH2Cl2, was added 1-methyl imidazole (0.11 mL, 2.5 equiv.) at 0-5 C. under nitrogen atmosphere. The reaction mixture was stirred for 10 min at 0-5 C. and then added methane sulfonyl chloride (0.05 mL, 1.2 equiv) at the same temperature. It was stirred for 1 h at 0-50 C. Then 6-methylpyridin-2-amine (58 mg, 1 equiv) was added, and stirred for 18h at room temperature. Water (15 mL) was added to the reaction mixture, layers were separated and aqueous layer was extracted with DCM (3×15 mL). The combined organic layer was washed with 1N HCl (15 mL), followed by Sat NaHCO3 (15 mL) and then with brine (10 mL). Combined organic layer was dried over Na2SO4, concentrated and purified by ISCO (silica gel, eluted by 5% MeOH in DCM gradient) to obtained 171 mg (99%) of titled compound as a clear oil.
  • 6
  • [ 1142197-14-5 ]
  • 6-bromo-N-(tert-butyl)-3-cyclopropylpyridin-2-amine [ No CAS ]
  • 7
  • [ 1142197-14-5 ]
  • 6-bromo-3-cyclopropylpyridin-2-ylamine [ No CAS ]
  • 8
  • [ 1142197-14-5 ]
  • tert-butyl (1R,2S,5S)-2-((6-bromo-3-cyclopropylpyridin-2-yl)carbamoyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate [ No CAS ]
  • 9
  • [ 1142197-14-5 ]
  • (1R,2S,5S)-N-(6-bromo-3-cyclopropylpyridin-2-yl)-3-azabicyclo[3.1.0]hexane-2-carboxamide trifluoroacetate salt [ No CAS ]
  • 10
  • [ 893738-68-6 ]
  • [ 1142197-14-5 ]
YieldReaction ConditionsOperation in experiment
76% With copper(ll) bromide; isopentyl nitrite; at 25.0℃; for 24h;Inert atmosphere; General procedure: Aminopyridine (1 mmol) and corresponding Cu(II) halide (0.5 mmol) were dissolveddibromo(chloro)methane (6 mL) at 25 C under an argon atmosphere. Alkyl nitrite (1.1 mmol)was added dropwise over 5 min and reaction mixture stirred at the appropriate temperature(Table 1 and 2) until GC-MS analysis of the reaction mixture indicated full consumption the of starting material. The reaction mixture was poured into 1 N NaOH (20 mL), stirred for 1 h andextracted with CH2Cl2 (3 × 20 mL). The combined organic extracts were dried (Na2SO4) andevaporated to dryness. The crude product was purified by column chromatography on silica gel,eluting with CH2Cl2. 2-Bromo-5-cyclopropylpyridine (2a): yield 76%. Rf = 0.49. 1H NMR (400MHz, CDCl3) delta 8.17 (d, J = 2.4 Hz, 1H), 7.34 (d, J = 8.2 Hz, 1H), 7.15 (dd, J =8.2, 2.4 Hz, 1H), 1.89 - 1.82 (m, 1H), 1.10 - 0.98 (m, 2H), 0.75 - 0.64 (m,2H). 13C NMR (100 MHz, CDCl3) delta 148.6, 138.8, 138.7, 135.4, 127.5, 12.5,9.1. GC-MS: tR= 7.031 min (m/z (rel. in.)) 197 (43.52%), 199 (41.85%).
  • 11
  • [ 893738-68-6 ]
  • [ 110-46-3 ]
  • [ 1142197-14-5 ]
  • C16H17N3 [ No CAS ]
  • C13H19N [ No CAS ]
YieldReaction ConditionsOperation in experiment
80%Chromat.; 9%Chromat.; 7%Chromat. With copper(ll) bromide; at 65.0℃; for 1h;Inert atmosphere; General procedure: Aminopyridine (1 mmol) and corresponding Cu(II) halide (0.5 mmol) were dissolveddibromo(chloro)methane (6 mL) at 25 C under an argon atmosphere. Alkyl nitrite (1.1 mmol)was added dropwise over 5 min and reaction mixture stirred at the appropriate temperature(Table 1 and 2) until GC-MS analysis of the reaction mixture indicated full consumption the of starting material. The reaction mixture was poured into 1 N NaOH (20 mL), stirred for 1 h andextracted with CH2Cl2 (3 × 20 mL). The combined organic extracts were dried (Na2SO4) andevaporated to dryness. The crude product was purified by column chromatography on silica gel,eluting with CH2Cl2. 2-Bromo-5-cyclopropylpyridine (2a): yield 76%. Rf = 0.49. 1H NMR (400MHz, CDCl3) delta 8.17 (d, J = 2.4 Hz, 1H), 7.34 (d, J = 8.2 Hz, 1H), 7.15 (dd, J =8.2, 2.4 Hz, 1H), 1.89 - 1.82 (m, 1H), 1.10 - 0.98 (m, 2H), 0.75 - 0.64 (m,2H). 13C NMR (100 MHz, CDCl3) delta 148.6, 138.8, 138.7, 135.4, 127.5, 12.5,9.1. GC-MS: tR= 7.031 min (m/z (rel. in.)) 197 (43.52%), 199 (41.85%).
  • 12
  • [ 893738-68-6 ]
  • [ 110-46-3 ]
  • [ 1142197-14-5 ]
  • C13H19N [ No CAS ]
YieldReaction ConditionsOperation in experiment
80%Chromat.; 15%Chromat. With copper(ll) bromide; at 25.0℃; for 72h;Inert atmosphere; General procedure: Aminopyridine (1 mmol) and corresponding Cu(II) halide (0.5 mmol) were dissolveddibromo(chloro)methane (6 mL) at 25 C under an argon atmosphere. Alkyl nitrite (1.1 mmol)was added dropwise over 5 min and reaction mixture stirred at the appropriate temperature(Table 1 and 2) until GC-MS analysis of the reaction mixture indicated full consumption the of starting material. The reaction mixture was poured into 1 N NaOH (20 mL), stirred for 1 h andextracted with CH2Cl2 (3 × 20 mL). The combined organic extracts were dried (Na2SO4) andevaporated to dryness. The crude product was purified by column chromatography on silica gel,eluting with CH2Cl2. 2-Bromo-5-cyclopropylpyridine (2a): yield 76%. Rf = 0.49. 1H NMR (400MHz, CDCl3) delta 8.17 (d, J = 2.4 Hz, 1H), 7.34 (d, J = 8.2 Hz, 1H), 7.15 (dd, J =8.2, 2.4 Hz, 1H), 1.89 - 1.82 (m, 1H), 1.10 - 0.98 (m, 2H), 0.75 - 0.64 (m,2H). 13C NMR (100 MHz, CDCl3) delta 148.6, 138.8, 138.7, 135.4, 127.5, 12.5,9.1. GC-MS: tR= 7.031 min (m/z (rel. in.)) 197 (43.52%), 199 (41.85%).
  • 13
  • [ 109-99-9 ]
  • [ 893738-68-6 ]
  • [ 1142197-14-5 ]
  • C12H16BrNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
45%Chromat.; 49%Chromat. With copper(ll) bromide; isopentyl nitrite; In acetonitrile; at 25.0℃; for 3h;Inert atmosphere; General procedure: Aminopyridine (1 mmol) and corresponding Cu(II) halide (0.5 mmol) were dissolved dibromo(chloro)methane (6 mL) at 25 C under an argon atmosphere. Alkyl nitrite (1.1 mmol)was added dropwise over 5 min and reaction mixture stirred at the appropriate temperature(Table 1 and 2) until GC-MS analysis of the reaction mixture indicated full consumption the of starting material. The reaction mixture was poured into 1 N NaOH (20 mL), stirred for 1 h and extracted with CH2Cl2 (3 × 20 mL). The combined organic extracts were dried (Na2SO4) andevaporated to dryness. The crude product was purified by column chromatography on silica gel,eluting with CH2Cl2.
  • 14
  • [ 67-56-1 ]
  • [ 893738-68-6 ]
  • [ 1063960-83-7 ]
  • [ 1142197-14-5 ]
YieldReaction ConditionsOperation in experiment
80%Chromat.; 17%Chromat. With copper(ll) bromide; isopentyl nitrite; In acetonitrile; at 25.0℃; for 16h;Inert atmosphere; General procedure: Aminopyridine (1 mmol) and corresponding Cu(II) halide (0.5 mmol) were dissolved dibromo(chloro)methane (6 mL) at 25 C under an argon atmosphere. Alkyl nitrite (1.1 mmol)was added dropwise over 5 min and reaction mixture stirred at the appropriate temperature(Table 1 and 2) until GC-MS analysis of the reaction mixture indicated full consumption the of starting material. The reaction mixture was poured into 1 N NaOH (20 mL), stirred for 1 h and extracted with CH2Cl2 (3 × 20 mL). The combined organic extracts were dried (Na2SO4) andevaporated to dryness. The crude product was purified by column chromatography on silica gel,eluting with CH2Cl2.
  • 15
  • [ 123-91-1 ]
  • [ 893738-68-6 ]
  • [ 1142197-14-5 ]
  • 2-(2-(2-bromoethoxy)ethoxy)-5-cyclopropylpyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
42%Chromat.; 21% With copper(ll) bromide; isopentyl nitrite; In acetonitrile; at 25.0℃; for 16h;Inert atmosphere; General procedure: Aminopyridine (1 mmol) and corresponding Cu(II) halide (0.5 mmol) were dissolved dibromo(chloro)methane (6 mL) at 25 C under an argon atmosphere. Alkyl nitrite (1.1 mmol)was added dropwise over 5 min and reaction mixture stirred at the appropriate temperature(Table 1 and 2) until GC-MS analysis of the reaction mixture indicated full consumption the of starting material. The reaction mixture was poured into 1 N NaOH (20 mL), stirred for 1 h and extracted with CH2Cl2 (3 × 20 mL). The combined organic extracts were dried (Na2SO4) andevaporated to dryness. The crude product was purified by column chromatography on silica gel,eluting with CH2Cl2.
  • 16
  • [ 893738-68-6 ]
  • [ 75-05-8 ]
  • [ 1142197-14-5 ]
  • N-(5-cyclopropylpyridin-2-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
21%Chromat.; 58%Chromat. With copper(ll) bromide; isopentyl nitrite; at 65.0℃; for 72h;Inert atmosphere; General procedure: Aminopyridine (1 mmol) and corresponding Cu(II) halide (0.5 mmol) were dissolveddibromo(chloro)methane (6 mL) at 25 C under an argon atmosphere. Alkyl nitrite (1.1 mmol)was added dropwise over 5 min and reaction mixture stirred at the appropriate temperature(Table 1 and 2) until GC-MS analysis of the reaction mixture indicated full consumption the of starting material. The reaction mixture was poured into 1 N NaOH (20 mL), stirred for 1 h andextracted with CH2Cl2 (3 × 20 mL). The combined organic extracts were dried (Na2SO4) andevaporated to dryness. The crude product was purified by column chromatography on silica gel,eluting with CH2Cl2.
  • 17
  • [ 1072-97-5 ]
  • [ 1142197-14-5 ]
  • 18
  • [ 1072-97-5 ]
  • [ 1063960-83-7 ]
  • [ 1142197-14-5 ]
  • 19
  • [ 1072-97-5 ]
  • [ 1142197-14-5 ]
  • C12H16BrNO [ No CAS ]
  • 20
  • [ 1072-97-5 ]
  • [ 1142197-14-5 ]
  • 2-(2-(2-bromoethoxy)ethoxy)-5-cyclopropylpyridine [ No CAS ]
  • 21
  • [ 1072-97-5 ]
  • [ 1142197-14-5 ]
  • C13H19N [ No CAS ]
  • 22
  • [ 1142197-14-5 ]
  • (2S,4S)-tert-butyl 2-((6-bromo-3-cyclopropylpyridin-2-yl)carbamoyl)-4-((dimethylamino)methyl)-4-fluoropyrrolidine-1-carboxylate [ No CAS ]
  • 23
  • [ 1142197-14-5 ]
  • (2S,4R)-N-(6-bromo-3-cyclopropylpyridin-2-yl)-4-((dimethylamino)methyl)-4-fluoropyrrolidine-2-carboxamide trifluoroacetate [ No CAS ]
  • 24
  • [ 1142197-14-5 ]
  • (2S,4S)-1-(2-(3-acetyl-5-(2-methylpyrimidin-5-yl)-1-indazol-1-yl)acetyl)-N-(6-bromo-3-cyclopropylpyridin-2-yl)-4-((dimethylamino)methyl)-4-fluoropyrrolidine-2-carboxamide [ No CAS ]
  • 25
  • [ 1142197-14-5 ]
  • tert-butyl (2S,4R)-2-((6-bromo-3-cyclopropylpyridin-2-yl)carbamoyl)-4-fluoropyrrolidine-1-carboxylate [ No CAS ]
  • 26
  • [ 1142197-14-5 ]
  • (2S,4R)-N-(6-bromo-3-cyclopropylpyridin-2-yl)-4-fluoropyrrolidine-2-carboxamide hydrochloride [ No CAS ]
  • 27
  • [ 1142197-14-5 ]
  • (2S,4R)-1-(2-(3-acetyl-5-(2-methylpyrimidin-5-yl)-1H-indazol-1-yl)acetyl)-N-(6-bromo-3-cyclopropylpyridin-2-yl)-4-fluoropyrrolidine-2-carboxamide [ No CAS ]
  • 28
  • [ 1142197-14-5 ]
  • tert-butyl (1R,3S,5R)-3-((6-bromo-3-cyclopropylpyridin-2-yl)carbamoyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate [ No CAS ]
  • 29
  • [ 1142197-14-5 ]
  • (1R,3S,5R)-N-(6-bromo-3-cyclopropylpyridin-2-yl)-2-azabicyclo[3.1.0]hexane-3-carboxamide hydrochloride [ No CAS ]
  • 30
  • [ 1142197-14-5 ]
  • (1R,3S,5R)-2-(2-(3-acetyl-5-(2-methylpyrimidin-5-yl)-1H-indazol-1-yl)acetyl)-N-(6-bromo-3-cyclopropyl-pyridin-2-yl)-2-azabicyclo[3.1.0]hexane-3-carboxamide [ No CAS ]
  • 31
  • [ 1142197-14-5 ]
  • tert-butyl (1R,3S,5R)-3-((6-bromo-3-cyclopropylpyridin-2-yl)carbamoyl)-5-methyl-2-azabicyclo[3.1.0]hexane-2-carboxylate [ No CAS ]
  • 32
  • [ 1142197-14-5 ]
  • 5-methyl-2-aza-bicyclo[3.1.0]hexane-3-carboxylic acid (6-bromo-3-cyclopropyl-pyridin-2-yl)-amide hydrochloride [ No CAS ]
  • 33
  • [ 1142197-14-5 ]
  • (1R,3S,5R)-2-(2-(3-acetyl-5-(2-methylpyrimidin-5-yl)-1H-indazol-1-yl)acetyl)-N-(6-bromo-3-cyclopropylpyridin-2-yl)-5-methyl-2-azabicyclo[3.1.0]hexane-3-carboxamide [ No CAS ]
  • 34
  • [ 1142197-14-5 ]
  • 5-cyclopropyl-2-iodopyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With copper(l) iodide; sodium iodide; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 130.0℃; for 2h; 39.1 5-cyclopropyl-2-iodopyridine <strong>[1142197-14-5]2-bromo-5-cyclopropylpyridine</strong> (purchased from Combi-Phos) (500 mg, 2.52 mmol) is dissolved in 5 mL of dioxane. Copper (I) iodide (96.2 mg, 0.50 mmol), sodium iodide (946 mg, 6.31 mmol) and N,N'-dimethylethylenediamine (105 mg, 1.01 mmol) are added and the mixture is stirred at 130 C. for 2 hours. Ethyl acetate is added and the mixture is washed with half concentrated aqueous sodium bicarbonate solution. The organic phase is dried and concentrated under reduced pressure. Yield: 541 mg (87% of theory) Mass spectrometry (ESI+): m/z=245 [M+H]+
 

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