HCID 11234748, compound → HCID 11464494, compound

HRID 494875Notes

Reaction equation

HRID 494875 reaction equation
CON(C)[C:4](=[O:28])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[CH:12]=[CH:13][C:14]3[O:18][C:17]([CH2:19][CH2:20][N:21]4[CH2:25][CH2:24][CH2:23][C@H:22]4[CH3:26])=[CH:16][C:15]=3[CH:27]=2)[CH:6]=1.[F:30][C:31]1[CH:32]=[C:33]([Mg]Br)[CH:34]=[CH:35][CH:36]=1>>[F:30][C:31]1[CH:32]=[C:33]([C:4]([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([C:11]3[CH:12]=[CH:13][C:14]4[O:18][C:17]([CH2:19][CH2:20][N:21]5[CH2:25][CH2:24][CH2:23][C@H:22]5[CH3:26])=[CH:16][C:15]=4[CH:27]=3)[CH:6]=2)=[O:28])[CH:34]=[CH:35][CH:36]=1

Participants

3

Reactant 2

HCID 11234748HCID 11234748, compoundHCID 178505773HCID 178505773, compound

Product 1

HCID 11464494HCID 11464494, compoundYield 46%

Procedure

The product from Example 145 and 3-fluorophenylmagnesium bromide were processed as described in Example 146 to provide the title compound (46% yield). MS (ESI APCI) m/z 428 (M+H)+; 1HNMR (300 MHz, CD3OD) δ 1.17 (d, 3H), 1.36-1.53 (m, 1H), 1.72-1.86 (m, 2H), 1.94-2.07 (m, 1H), 2.22-2.33 (m, 1H), 2.39-2.58 (m, 2H), 2.93-3.14 (m, 2H), 3.18-3.3 (m, 2H), 6.62 (s, 1H), 7.37-7.45 (m, 1H), 7.49-7.52 (m, 2H), 7.52-7.66 (m, 4H), 7.72 (ddd, 1H), 7.77 (dd, 1H), 7.94 (ddd, 1H), 8.02 (dd, 1H).

Sources & evidence

ORD record
ord-94a9742c15c843a3b593cc9abeaea99c
Source dataset
uspto-grants-2009_05
Patent number
US07538138B2

Reaction notes

Loading…