Acrylamide → HCID 86702545, compound

HRID 877071Notes

Reaction equation

HRID 877071 reaction equation
[C:1]([O:5][C:6](=[O:38])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:31]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[CH:30][N:21]4[N:22]=[C:23]5[C:28]([CH:27]=[CH:26][CH:25]=[C:24]5Br)=[C:20]4[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[C:39]([NH2:43])(=[O:42])[CH:40]=[CH2:41].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:31]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[CH:30][N:21]4[N:22]=[C:23]5[C:28]([CH:27]=[CH:26][CH:25]=[C:24]5/[CH:41]=[CH:40]/[C:39]([NH2:43])=[O:42])=[C:20]4[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)=[O:38])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6579AcrylamideHCID 80271Tri-o-tolylphosphineHCID 86702541HCID 86702541, compound

Product 1

HCID 86702545HCID 86702545, compoundYield 143%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

200 mg (0.351 mmol) {1-[4-(7-Bromo-3-phenylpyrimido[1,2-b]indazol-2-yl)phenyl]-cyclobutyl}carbamic acid tert-butyl ester (intermediate example Int-2-1), 49.9 mg (0.7 mmol) acrylamide, 18.2 mg (0.06 mmol) tri-2-tolylphosphane and 7.9 mg (0.035 mmol) palladium(II) acetate were treated in 2.47 mL degassed acetonitrile as described in example 13 (step 1). After the work-up 281 mg (>100%) of the crude product were obtained and used in the next step without further purification.

Workup

  1. customdegassed acetonitrile

Sources & evidence

ORD record
ord-489a8f80ac6e49a09eddb0d4880edee9
Source dataset
uspto-grants-2015_03
Patent number
US08987286B2

Reaction notes

Loading…