(6-Bromo-4-(3-(2-(pyrrolidin-1-yl)ethyl)phenylamino)quinolin-3-yl)(cyclopropyl)methanone → HCID 66715491, compound

HRID 2271968Notes

Reaction equation

HRID 2271968 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([CH:14]1[CH2:16][CH2:15]1)=[O:13])=[C:5]2[NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][CH2:25][N:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)[CH:19]=1.[Cl:31][C:32]1[CH:37]=[C:36](B2OC(C)(C)C(C)(C)O2)[CH:35]=[C:34]([F:47])[C:33]=1[OH:48]>>[Cl:31][C:32]1[CH:37]=[C:36]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:12]([CH:14]2[CH2:16][CH2:15]2)=[O:13])=[C:5]3[NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][CH2:25][N:26]3[CH2:27][CH2:28][CH2:29][CH2:30]3)[CH:19]=2)[CH:35]=[C:34]([F:47])[C:33]=1[OH:48]

Participants

3

Reactant 2

HCID 66715504(6-Bromo-4-(3-(2-(pyrrolidin-1-yl)ethyl)phenylamino)quinolin-3-yl)(cyclopropyl)methanoneHCID 667160792-Chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Product 1

HCID 66715491HCID 66715491, compoundYield 32%

Procedure

Following general procedure A-1, {6-bromo-4-[3-(2-(pyrrolidin-1-yl)ethyl)phenylamino]quinolin-3-yl}(cyclopropyl)methanone (56 mg, 0.120 mmol) was reacted with 2-chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (49 mg, 0.180 mmol) to afford the desired product (20 mg, 32%) as a yellow solid: 1H NMR (500 MHz, CD3OD+TFA-d) δ 9.45 (s, 1H), 8.22 (dd, J=8.8, 1.9 Hz, 1H), 8.02 (d, J=8.8 Hz, 1H), 7.91 (s, 1H), 7.65-7.58 (m, 1H), 7.54 (d, J=7.8, 1H), 7.46 (s, 1H), 7.38 (d, J=7.8 Hz, 1H), 7.12 (dd, 11.5, 2.3 Hz, 1H), 6.95 (s, 1H), 3.72-3.64 (m, 2H), 3.45-3.36 (m, 2H), 3.17-3.05 (m, 4H), 2.92-2.83 (m, 1H), 2.20-2.09 (m, 2H), 2.08-1.99 (m, 2H), 1.31-1.16 (m, 4H); ESI MS m/z 530 [C31H29ClFN3O2+H]+; HPLC>99% (AUC), tR=10.82 min.

Sources & evidence

ORD record
ord-646a1f46fae34f909c506e691b1f33bf
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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