Methyl 4-(4-bromobutoxy)benzoate → 4-{4-[1-(2,2-Dimethyl-propyl)-4-propyl-1h-indol-5-yloxy]-butoxy}-benzoic acid

HRID 2423553Notes

Reaction equation

HRID 2423553 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13]C)=[O:12])=[CH:9][CH:8]=1.[CH3:17][C:18]([CH3:34])([CH3:33])[CH2:19][N:20]1[C:28]2[C:23](=[C:24]([CH2:30][CH2:31][CH3:32])[C:25]([OH:29])=[CH:26][CH:27]=2)[CH:22]=[CH:21]1>>[CH3:17][C:18]([CH3:33])([CH3:34])[CH2:19][N:20]1[C:28]2[C:23](=[C:24]([CH2:30][CH2:31][CH3:32])[C:25]([O:29][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]3[CH:16]=[CH:15][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=3)=[CH:26][CH:27]=2)[CH:22]=[CH:21]1

Participants

3

Reactant 2

HCID 10979046Methyl 4-(4-bromobutoxy)benzoateHCID 186724755-hydroxy-4-propyl-N-neopentylindole

Product 1

HCID 119523454-{4-[1-(2,2-Dimethyl-propyl)-4-propyl-1h-indol-5-yloxy]-butoxy}-benzoic acid

Procedure

Similar procedures as outlined in examples 1 & 26 were followed using methyl 4-(4-bromobutoxy)benzoate and 1-(2,2-dimethylpropyl)-4-propyl-1H-indol-5-ol. 1H NMR (500 MHz, DMSO) δ 12.64 (s, 1H), 7.92 (d, 2H), 7.24 (d, 1H), 7.20 (s, 1H), 7.02 (d, 2H), 6.87 (d, 1H), 6.37 (d, 1H), 4.14 (t, 2H), 4.01 (t, 2H), 3.90 (s, 2H), 2.77 (t, 2H), 1.95 (m, 2H), 1.88 (m, 2H), 1.59 (m, 2H), 0.92 (s, 9H), 0.90 (t, 3H). MS (ESI): 438 (M+H).

Sources & evidence

ORD record
ord-3efbe1afa27d41c782acecd46f1e8f20
Source dataset
uspto-grants-2011_06
Patent number
US07960417B2

Reaction notes

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