Tetramethyltin → HCID 21183003, compound

HRID 1070335Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:14]([C:16]2[C:17]3[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][C:18]=3[S:19][C:20]=2[C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][N:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)=[CH:23][CH:22]=2)=[O:15])[CH:5]=[CH:6][C:7]=1[CH2:8][N:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1.[CH3:40][Sn](C)(C)C.CCN(CC)CC.CO.CCOC(C)=O>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:40][C:2]1[CH:3]=[C:4]([C:14]([C:16]2[C:17]3[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][C:18]=3[S:19][C:20]=2[C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][N:30]3[CH2:31][CH2:32][CH2:33][CH2:34]3)=[CH:23][CH:22]=2)=[O:15])[CH:5]=[CH:6][C:7]=1[CH2:8][N:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

Conditions

Temperature: 135 °C

Procedure

To a solution of 6-hydroxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl 3-bromo-4-[(1-pyrrolidinyl)methyl]phenyl ketone (Example 137, Part D) (81 mg, 0.13 mmol) in DMF (2 mL) in a pressure tube were added tetrakis(triphenylphosphine)palladium(0) (18 mg) and tetramethyltin (0.3 mL) sequentially, followed by flushing with argon. The mixture was allowed to stir in the sealed pressure tube at 135° C. for 23 h in dark. The cooled reaction mixture was fractionated directly through flash chromatography with Et3N:MeOH:EtOAc (5:10:85) to afford the title compound (32 mg, 44%).

Workup

customby flushing with argon
customThe cooled reaction mixture

Sources & evidence

ORD record: ord-69e6b418ae814a7581583fafc605cb88
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06251921B1

Reaction notes

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