4-Fluorophenethyl bromide → HCID 71209347, compound

HRID 1912563Notes

Reaction equation

HRID 1912563 reaction equation
[C:1]([O:5][CH:6]([C:11]1[C:12]([C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[O:27][CH2:26][CH2:25][CH2:24]3)=[C:13]2[CH:20]=[CH:19][NH:18][C:14]2=[N:15][C:16]=1[CH3:17])[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].Br[CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=1>>[C:1]([O:5][CH:6]([C:11]1[C:12]([C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[O:27][CH2:26][CH2:25][CH2:24]3)=[C:13]2[CH:20]=[CH:19][N:18]([CH2:32][CH2:33][C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=3)[C:14]2=[N:15][C:16]=1[CH3:17])[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 5731534-Fluorophenethyl bromideHCID 71209024methyl 2-(tert-butoxy)-2-(4-(chroman-6-yl)-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)acetate

Product 1

HCID 71209347HCID 71209347, compound

Procedure

The title compound was prepared in a manner similar to that described in Example 27, Step H from methyl 2-(tert-butoxy)-2-(4-(chroman-6-yl)-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)acetate and 1-(2-bromoethyl)-4-fluorobenzene. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.46 (d, J=1.6 Hz, 1 H), 7.18-7.07 (m, 3 H), 6.99-6.89 (m, 4 H), 6.31 (dd, J=3.5, 7.6 Hz, 1 H), 5.52 (d, J=6.0 Hz, 1 H), 4.82-4.73 (m, 1 H), 4.68-4.58 (m, 1 H), 4.30 (t, J=5.1 Hz, 2 H), 3.16 (tq, J=7.0, 14.3 Hz, 2 H), 2.94-2.77 (m, 5 H), 2.15-2.04 (m, 2 H), 0.99-0.89 (s, 9 H); LC/MS (m/z) ES+=517.4 (M+1).

Sources & evidence

ORD record
ord-97269737b4ee4aca92cacbbe54c5ffd1
Source dataset
uspto-grants-2013_12
Patent number
US08609653B2

Reaction notes

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