Tributylvinyltin → N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-7-vinylthieno[2,3-b]pyrazine-6-carboxamide

HRID 1184855Notes

Reaction equation

HRID 1184855 reaction equation
Br[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][N:9]=2)[S:4][C:3]=1[C:11]([NH:13][C:14]1[CH:19]=[C:18]([NH:20][C:21](=[O:33])[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([C:31]#[N:32])([CH3:30])[CH3:29])[CH:23]=2)[CH:17]=[CH:16][C:15]=1[CH3:34])=[O:12].[CH2:35]([Sn](CCCC)(CCCC)C=C)[CH2:36]CC>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:31]([C:28]([C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[C:21]([NH:20][C:18]1[CH:17]=[CH:16][C:15]([CH3:34])=[C:14]([NH:13][C:11]([C:3]2[S:4][C:5]3=[N:6][CH:7]=[CH:8][N:9]=[C:10]3[C:2]=2[CH:35]=[CH2:36])=[O:12])[CH:19]=1)=[O:33])([CH3:30])[CH3:29])#[N:32]

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 671255437-bromo-N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide

Product 1

HCID 67125664N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-7-vinylthieno[2,3-b]pyrazine-6-carboxamideYield 10.1%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution of 7-bromo-N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide 42 (22 mg, 0.041 mmol), bis(triphenylphosphine)palladium(II) chloride (1.445 mg, 2.058 μmol) and tributyl(vinyl)tin (0.024 mL, 0.082 mmol) in toluene (1 mL) was stirred for 30 min at 110° C. in microwave. After filtration, diluted with toluene and washed with water, brine, dried and evaporated. Purification by HPLC gave the title compound N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-7-vinylthieno[2,3-b]pyrazine-6-carboxamide 43c (2 mg, 10.09%). NMR (400 MHz, DMSO-d6) 2.27 (s, 3H), 5.76 (dd, J=12.0 and 2.3 Hz, 1H), 8.85-8.91 (dd, J=17.6 and 1.9 Hz, 1H), 7.28-7.38 (m, 2H), 7.58-7.68 (m, 2H), 7.76 (d, J=7.8 Hz, 1H), 7.91 (d, J=1.9 Hz, 1H), 7.96 (d, J=7.8 Hz, 1H), 8.05 (t, J=1.9 Hz, 1H), 8.80 (d, J=2.3, 1H), 8.94 (d, J=2.3 Hz, 1H), 10.37 (s, 1H), 10.38 (s, 1H). (m/z)=482 (M+H)+.

Workup

  1. filtrationAfter filtration
  2. additiondiluted with toluene
  3. washwashed with water, brine
  4. customdried
  5. customevaporated
  6. customPurification by HPLC

Sources & evidence

ORD record
ord-68498e5270f44c11b979276df7b0101c
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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