Sodium Hydroxide → HCID 56839776, compound

HRID 1466890Notes

Reaction equation

HRID 1466890 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([S:18][C:19]3[CH:20]=[C:21]([B:25]4[O:33]C(C)(C)C(C)(C)[O:26]4)[CH:22]=[CH:23][CH:24]=3)=[C:7]([CH3:17])[N:8]2[C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1.CO>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([S:18][C:19]3[CH:20]=[C:21]([B:25]([OH:33])[OH:26])[CH:22]=[CH:23][CH:24]=3)=[C:7]([CH3:17])[N:8]2[C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131732694HCID 131732694, compound

Product 1

HCID 56839776HCID 56839776, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

3-(6-Chloro-2-methyl-1-pyridin-3-yl-1H-indol-3-ylsulfanyl)-phenylboronic acid pinacol ester (0.400 g, 0.86 mmol) was dissolved in THF:MeOH (1:1, 10 mL) and sodium hydroxide (2.5 mL of 1.0M aqueous solution, 2.5 mmol) was added. The reaction was stirred at room temperature overnight then submitted to aqueous workup and purified by preparatory HPLC (30-100% ACN in H2O) to afford the title compound.

Workup

  1. custompurified by preparatory HPLC (30-100% ACN in H2O)

Sources & evidence

ORD record
ord-e66aeec127d24084ab5a5c56a522da36
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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