Water → HCID 22603403, compound

HRID 2307927Notes

Reaction equation

CC(C)([O-])C.[K+].[NH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.Br[C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([Cl:31])[CH:25]=2)[C:15]=1[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33].O>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:31][C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][C:27]=1[Cl:30])[CH2:23][N:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14]([N:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)=[C:15]1[C:32]([O:34][C:35]([CH3:38])([CH3:36])[CH3:37])=[O:33]

Participants

Conditions

Temperature: 90 °C

Procedure

Pd2(dba)3 (114 mg), R-BINAP (69 mg), potassium t-butoxide (294 mg), and morpholine (0.209 ml) were added to a solution of t-butyl 3-bromo-N-(3,4-dichlorobenzyl)indole-2-carboxylate (1 g) in de-gassed toluene (6 ml), under an atmosphere of argon. The reaction was stirred and heated at 90° C. for 16 hours then poured into water (50 ml), extracted with ethyl acetate (3×50 ml), and the combined organic extracts were dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography using 10% ethyl acetate:iso-hexane as eluent, to afford the product as a yellow oil (325 mg, 33%); NMR d (CD3SOCD3) 3.20 (t, 4H), 3.73 (t, 4H), 5.56 (s, 2H), 6.88 (d, 1H), 7.7 (t, 1H), 7.25 (m, 2H), 7.50 (m, 2H), 7.80 (d, 1H), M/z (+) 461 (MH+), 405.

Workup

extractionextracted with ethyl acetate (3×50 ml)
dry with materialthe combined organic extracts were dried (MgSO4)
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-9f6eb6381b914962a3313d8029c9b0b4
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06833387B1

Reaction notes

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