Allyltributylstannane → tert-butyl 2-allyl-3-(2-methoxy-2-oxoethyl)-1H-indole-1-carboxylate

HRID 1471644Notes

Reaction equation

Br[C:2]1[N:3]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:4]2[C:9]([C:10]=1[CH2:11][C:12]([O:14][CH2:15]C)=[O:13])=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH2:24]([Sn](CCCC)(CCCC)CCCC)[CH:25]=[CH2:26]>CN(C=O)C.CCOC(C)=O.O.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>[CH2:26]([C:2]1[N:3]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[C:4]2[C:9]([C:10]=1[CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:25]=[CH2:24]

Participants

Conditions

Temperature: 80 °C

Procedure

Argon was bubbled into a solution of tert-butyl 2-bromo-3-(2-ethoxy-2-oxoethyl)-1H-indole-1-carboxylate (3.68 g, 9.66 mmol) in DMF (50 mL) for 1 h. Allyltributyltin (3 mL, 9.66 mmol) was added to the reaction mixture followed by the addition of Pd(PPh3)4 (1.1 g, 10 mol %). The reaction was heated at 80° C. for 6 h and then diluted with EtOAc and H2O. The entire solution was filtered over celite and to the solute was added 20% aqueous KH2PO4. The organics were separated and dried over sodium sulfate. After removal of solvent, the crude product was purified by silica gel chromatography to provide tert-butyl 2-allyl-3-(2-methoxy-2-oxoethyl)-1H-indole-1-carboxylate (2.52 g, 76%). MS (m/z) 330 [M+H]+.

Workup

filtrationThe entire solution was filtered over celite and to the solute
additionwas added 20% aqueous KH2PO4
customThe organics were separated
dry with materialdried over sodium sulfate
customAfter removal of solvent
customthe crude product was purified by silica gel chromatography

Sources & evidence

ORD record: ord-800ee988fa6a46ad8dafcc807a616157
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012441B2

Reaction notes

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