Carbon tetrabromide → HCID 58928846, compound

HRID 853612Notes

Reaction equation

HRID 853612 reaction equation
[CH:1]([O:14][C:15]1[C:16]2[C:29](=[O:30])[N:28]([CH2:31][C:32]3[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=3)[CH2:27][C:17]=2[C:18]([CH2:25]O)=[C:19]2[C:24]=1[N:23]=[CH:22][CH:21]=[CH:20]2)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Br)(Br)(Br)[Br:41].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH:1]([O:14][C:15]1[C:16]2[C:29](=[O:30])[N:28]([CH2:31][C:32]3[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=3)[CH2:27][C:17]=2[C:18]([CH2:25][Br:41])=[C:19]2[C:24]=1[N:23]=[CH:22][CH:21]=[CH:20]2)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 58928887HCID 58928887, compound

Product 1

HCID 58928846HCID 58928846, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

For example, 9-benzhydryloxy-5-hydroxymethyl-7-(4-methoxy-benzyl)-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one A11.5 prepared by the method shown in Example 50, is reacted in dichloromethane with one molar equivalent of carbon tetrabromide and triphenylphosphine to produce 9-benzhydryloxy-5-bromomethyl-7-(4-methoxy-benzyl)-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one A11.6. The product is then heated at 120° C. with an excess of a trialkyl phosphite A11.3. The resulting phosphonate is then deprotected to afford the phenolic product A11.7.

Sources & evidence

ORD record
ord-e336855ea243479abe867824233cdc2a
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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