4-(Bromomethyl)oxane → HCID 71209248, compound

HRID 1912588Notes

Reaction equation

HRID 1912588 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][CH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]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][CH:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)[C:14]2=[N:15][C:16]=1[CH3:17])[C:7]([OH:9])=[O:8])([CH3:3])([CH3:4])[CH3:2]

Participants

3

Reactant 2

HCID 27732864-(Bromomethyl)oxaneHCID 71209024methyl 2-(tert-butoxy)-2-(4-(chroman-6-yl)-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)acetate

Product 1

HCID 71209248HCID 71209248, 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 4-(bromomethyl)tetrahydro-2H-pyran. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.49-7.43 (m, 1 H), 7.20-7.11 (m, 2 H), 6.98 (t, J=8.3 Hz, 1 H), 6.45-6.39 (m, 1 H), 5.53 (d, J=4.3 Hz, 1 H), 4.51-4.41 (m, 1 H), 4.32 (t, J=5.2 Hz, 2 H), 4.24 (dd, J=7.9, 14.5 Hz, 1 H), 4.03-3.93 (m, 2 H), 3.45-3.33 (m, 2 H), 2.97-2.82 (m, 5 H), 2.29 (br. s., 1 H), 2.17-2.07 (m, 2 H), 1.64-1.55 (m, 1 H), 1.54-1.33 (m, 3 H), 1.00-0.90 (s, 9 H); LC/MS (m/z) ES+=493.38 (M+1).

Sources & evidence

ORD record
ord-8ebb6cb8ff8a47d1838fa6ae92bd60aa
Source dataset
uspto-grants-2013_12
Patent number
US08609653B2

Reaction notes

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