Diisobutylaluminum hydride → (E)-5-Fluoro-N-(8-(hydroxymethyl)-9-methyl-6,7-dihydro-5H-benzo[7]annulen-2-yl)picolinamide

HRID 1911043Notes

Reaction equation

HRID 1911043 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:10][C:11]2[CH:12]=[CH:13][C:14]3[CH2:20][CH2:19][CH2:18][C:17]([C:21](OC)=[O:22])=[C:16]([CH3:25])[C:15]=3[CH:26]=2)=[O:9])=[N:6][CH:7]=1.CC(C[AlH]CC(C)C)C>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:10][C:11]2[CH:12]=[CH:13][C:14]3[CH2:20][CH2:19][CH2:18][C:17]([CH2:21][OH:22])=[C:16]([CH3:25])[C:15]=3[CH:26]=2)=[O:9])=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 86685434(E)-Methyl 2-(5-fluoropicolinamido)-9-methyl-6,7-dihydro-5H-benzo[7]annulene-8-carboxylate

Product 1

HCID 86685435(E)-5-Fluoro-N-(8-(hydroxymethyl)-9-methyl-6,7-dihydro-5H-benzo[7]annulen-2-yl)picolinamide

Procedure

In a manner similar to the procedure of step 3B, (E)-methyl 2-(5-fluoropicolinamido)-9-methyl-6,7-dihydro-5H-benzo[7]annulene-8-carboxylate from step 43A was reduced with DIBAL to afford the titled compound of Step 43B. LCMS (M+H)+=327.2. 1H NMR (500 HMz, chloroform-d) δ 9.79 (s, 1H), 8.44 (d, J=2.7 Hz, 1H), 8.35-8.31 (m, 1H), 7.65 (d, J=2.3 Hz, 1H), 7.61-7.56 (m, 1H), 7.54 (dd, J=8.1, 2.3 Hz, 1H), 7.17 (d, J=8.1 Hz, 1H), 4.38 (s, 2H), 2.53 (t, J=7.0 Hz, 2H), 2.13 (s, 3H), 2.09 (quin, J=7.1 Hz, 2H), 2.02-1.95 (m, 3H).

Sources & evidence

ORD record
ord-e95d5f7768ae49c29a9521bbae7657ce
Source dataset
uspto-grants-2013_12
Patent number
US08604024B2

Reaction notes

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