Tributylvinyltin → 1-[(2-Methoxy-5-methylphenyl)sulfonyl]-4-vinylindoline

HRID 1159760Notes

Reaction equation

Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][N:6]2[S:11]([C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=1[O:21][CH3:22])(=[O:13])=[O:12].[CH2:23]([Sn](CCCC)(CCCC)C=C)[CH2:24]CC>C1(C)C=CC=CC=1>[CH3:22][O:21][C:15]1[CH:16]=[CH:17][C:18]([CH3:20])=[CH:19][C:14]=1[S:11]([N:6]1[C:7]2[C:3](=[C:2]([CH:23]=[CH2:24])[CH:10]=[CH:9][CH:8]=2)[CH2:4][CH2:5]1)(=[O:13])=[O:12]

Participants

Conditions

Temperature: 110 °C

Procedure

4-bromo-1-[(2-methoxy-5-methylphenyl)sulfonyl]indoline (tot 721 mg, 1.89 mmol; Intermediate 9), tributyl(vinyl)stannane (tot 1.10 mL, 3.78 mmol) and Pd(PPh3)2OAc2 (tot 142 mg, 0.19 mmol) in dry toluene (tot 12 mL) was distributed into 3 tubes and stirred at 110° C. using a STEM block over weekend (68 h). Still about 30% starting material. The reactions were combined, filtered and concentrated. Redissolved in dry MeCN (8 mL), distributed into 2 Micro wave tubes followed by addition of tributyl(vinyl)stannane (300 μL, 1.03 mmol) and Pd(PPh3)2OAc2 (30 mg, 0.04 mmol) to each tube. The mixtures were irradiated by micro waves 180° C. for 600 s. Filtration and concentration followed by purification by flash (30% hexane in DCM) gave the title compound (300 mg, 48%) as a colorless viscous oil. MS (ESI+) for C18H19NO3S m/z 330 (M+H)+.

Workup

custom(68 h)
filtrationfiltered
concentrationconcentrated
dissolutionRedissolved in dry MeCN (8 mL)
customThe mixtures were irradiated by micro waves 180° C. for 600 s
filtrationFiltration and concentration
customfollowed by purification by flash (30% hexane in DCM)

Sources & evidence

ORD record: ord-ec6e1621cfc64df6940283ccb45eeafa
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07812017B2

Reaction notes

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