Triethylamine → 3-Cyano-4-methoxymethyl-5-phenoxy-beta-carboline

HRID 2166361Notes

Reaction equation

BrBr.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:22]([C:29]1[CH:41]=[CH:40][CH:39]=[C:38]2[C:30]=1[C:31]1[C:32]([CH2:45][O:46][CH3:47])=[C:33]([C:42]([NH2:44])=O)[N:34]=[CH:35][C:36]=1[NH:37]2)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C>C(Cl)Cl.O>[O:22]([C:29]1[CH:41]=[CH:40][CH:39]=[C:38]2[C:30]=1[C:31]1[C:32]([CH2:45][O:46][CH3:47])=[C:33]([C:42]#[N:44])[N:34]=[CH:35][C:36]=1[NH:37]2)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1.1 g of Br2 in 10 ml of methylene chloride is put in drop by drop into a stirred solution of 1.8 g (15 mmol) of triphenylphosphine in 50 ml of methylene chloride at 0° C. Then, 2 g of 5-phenoxy-4-methoxymethyl-beta-carboline-3-carboxamide and 1.9 ml of triethylamine are added. The reaction mixture is stirred for 1 hour at 0° C. and then vigorously stirred with 25 ml of methylene chloride and 25 ml of water for 5 minutes. After removal of the aqueous phase from the organic phase by concentration, 0.8 g of the desired product is obtained.

Workup

customAfter removal of the aqueous phase from the organic phase
concentrationby concentration

Sources & evidence

ORD record: ord-0a6a047c07b047d6914465e4502beddb
Source dataset: uspto-grants-1990_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04945090

Reaction notes

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