HCID 86689576, compound → HCID 86689577, compound

HRID 1853938Notes

Reaction equation

HRID 1853938 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:32]2[CH2:36][CH2:35][C@H:34]([NH:37]C(=O)OC(C)(C)C)[CH2:33]2)[CH:5]=[CH:6][C:7]=1[N:8]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:9]([C:11]1[S:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[CH:14][CH:15]=1)=[O:10]>CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[NH2:37][C@H:34]1[CH2:35][CH2:36][N:32]([C:4]2[CH:3]=[CH:2][C:7]3[N:8]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:30])([CH3:31])[CH3:29])[C:9](=[O:10])[C:11]4[S:12][C:13]([C:16]5[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=5)=[CH:14][C:15]=4[C:6]=3[CH:5]=2)[CH2:33]1

Participants

3

Reactant 1

HCID 86689576HCID 86689576, compound

Product 1

HCID 86689577HCID 86689577, compoundYield 16.5%

Reagents, catalysts & solvents 1

HCID 178418851HCID 178418851, compoundCatalyst

Procedure

Following Step 3 from General Procedure A, (S)-tert-butyl 1-{3-bromo-4-[5-(4-methoxyphenyl)-N-{[2-(trimethylsilyl)ethoxy]methyl}thiophene-2-carboxamido]phenyl}pyrrolidin-3-ylcarbamate (210 mg, 0.29 mmol) was reacted with bis(tri-tert-butylphosphine)palladium (15 mg, 0.029 mmol) to afford the desired product (25 mg, 14%): ESI MS m/z 622 [C28H35N3O3SSi+H]+.

Sources & evidence

ORD record
ord-271b33aec29b4dd1814463b0b21cd26a
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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