tert-Butyl 4-(bromomethyl)piperidine-1-carboxylate → HCID 71209426, compound

HRID 1912587Notes

Reaction equation

HRID 1912587 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][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[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][N:36]([C:39]([O:41][C:42]([CH3:43])([CH3:45])[CH3:44])=[O:40])[CH2:35][CH2:34]3)[C:14]2=[N:15][C:16]=1[CH3:17])[C:7]([OH:9])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 15512811tert-Butyl 4-(bromomethyl)piperidine-1-carboxylateHCID 71209024methyl 2-(tert-butoxy)-2-(4-(chroman-6-yl)-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)acetate

Product 1

HCID 71209426HCID 71209426, 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 tert-butyl 4-(bromomethyl)piperidine-1-carboxylate. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.48-7.42 (m, 1 H), 7.21-7.14 (m, 1 H), 7.12-7.08 (m, 1 H), 6.95 (dd, J=4.9, 8.4 Hz, 1 H), 6.33 (dd, 1 H), 5.53 (d, J=3.7 Hz, 1 H), 4.30 (t, J=5.2 Hz, 2 H), 4.13 (dd, J=7.0, 14.2 Hz, 3 H), 3.50 (s, 1 H), 2.98-2.77 (m, 5 H), 2.67 (br. s., 2 H), 2.25-2.14 (m, 1 H), 2.14-2.02 (m, 2 H), 1.64 (d, J=12.7 Hz, 1 H), 1.56 (br. s., 1 H), 1.50-1.42 (m, 10 H), 1.31-1.13 (m, 2 H), 0.99-0.89 (s, 9 H); LC/MS (m/z) ES+=592.32 (M+1).

Sources & evidence

ORD record
ord-6d9938c2f1034a4f8286536aafbd1da1
Source dataset
uspto-grants-2013_12
Patent number
US08609653B2

Reaction notes

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