Sodium hydride → (4S,6S)-6-[3,5-bis(trifluoromethyl)phenyl]-3-[(6-iodo-2,3-dihydro-1H-inden-5-yl)methyl]-4-methyl-1,3-oxazinan-2-one

HRID 537980Notes

Reaction equation

HRID 537980 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:18][C:17](=[O:19])[NH:16][C@@H:15]([CH3:20])[CH2:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[H-].[Na+].Br[CH2:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][C:35]=1[I:36])[CH2:32][CH2:31][CH2:30]2>>[F:22][C:2]([F:1])([F:21])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:18][C:17](=[O:19])[N:16]([CH2:26][C:27]3[CH:28]=[C:29]4[C:33](=[CH:34][C:35]=3[I:36])[CH2:32][CH2:31][CH2:30]4)[C@@H:15]([CH3:20])[CH2:14]2)[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 575443555-(Bromomethyl)-6-iodoindane2×HCID 57544409(4S,6S)-6-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazinan-2-one2×

Product 1

HCID 57544368(4S,6S)-6-[3,5-bis(trifluoromethyl)phenyl]-3-[(6-iodo-2,3-dihydro-1H-inden-5-yl)methyl]-4-methyl-1,3-oxazinan-2-one

Procedure

(4S,6S)-6-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazinan-2-one (Intermediate 22; 104 mg; 0.318 mmol) was treated with sodium hydride (60% in oil; 11.9 mg; 0.297 mmol) and 5-(bromomethyl)-6-iodoindane (Intermediate 24; 100 mg; 0.297 mmol) as described for Intermediate 23 to afford (4S,6S)-6-[3,5-bis(trifluoromethyl)phenyl]-3-[(6-iodo-2,3-dihydro-1H-inden-5-yl)methyl]-4-methyl-1,3-oxazinan-2-one as a white solid. LCMS=583.8 (M+1)+. 1H NMR (CDCl3, 500 MHz): δ 7.90 (s, 2H), 7.87 (s, 1H), 7.72 (s, 1H), 7.19 (s, 1H), 5.43 (dd, J=11.8, 1.7 Hz, 1H), 4.96 (d, J=15-8 Hz, 1H), 4.47 (d, J=16 Hz, 1H), 3.69-3.62 (m, 1H), 2.90-2.86 (m, 4H), 2.43-2.38 (m, 1H), 2.12-2.05 (m, 2H), 2.00-1.92 (m, 1H), 1.25 (d, J=6.2 Hz, 3H).

Sources & evidence

ORD record
ord-488e06cf41a843c78bd4abcb281f3bca
Source dataset
uspto-grants-2014_10
Patent number
US08865707B2

Reaction notes

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