2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 86692984, compound

HRID 2271922Notes

Reaction equation

HRID 2271922 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:19]=[CH:20][C:21]([N:24]2[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]2)=[N:22][CH:23]=1.[Cl:37][C:38]1[CH:43]=[C:42](B2OC(C)(C)C(C)(C)O2)[CH:41]=[C:40]([Cl:53])[C:39]=1[OH:54]>>[CH:14]1([C:12]([C:6]2[CH:7]=[N:8][C:9]3[C:4]([C:5]=2[NH:17][C:18]2[CH:19]=[CH:20][C:21]([N:24]4[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:34])([CH3:35])[CH3:36])=[O:31])[CH2:26][CH2:25]4)=[N:22][CH:23]=2)=[CH:3][C:2]([C:42]2[CH:43]=[C:38]([Cl:37])[C:39]([OH:54])=[C:40]([Cl:53])[CH:41]=2)=[CH:11][CH:10]=3)=[O:13])[CH2:15][CH2:16]1

Participants

3

Reactant 2

HCID 667151272,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 68092004HCID 68092004, compound

Product 1

HCID 86692984HCID 86692984, compoundYield 100.2%

Procedure

Following general procedure F, tert-butyl 4-{5-[6-bromo-3-(cyclopropanecarbonyl)quinolin-4-ylamino]pyridin-2-yl}piperazine-1-carboxylate (65 mg, 0.118 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (51 mg, 0.177 mmol) to afford the crude product (75 mg) as an orange solid: ESI MS m/z 634 [C33H33C12N5O4+H]+.

Sources & evidence

ORD record
ord-495db9c7969e4fc99dbe78dec3311632
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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