Potassium Fluoride → N-tert-butyl-6-(3-cyano-1-cyclopentyl-5-fluoro-6-methyl-1H-indol-2-yl)pyridine-3-sulfonamide

HRID 1028014Notes

Reaction equation

[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([CH:12]3CC3)=[CH:9][CH:10]=2)[N:5]([CH:15]2[CH2:18][CH2:17][CH2:16]2)[C:4]=1B(O)O)#[N:2].[C:22]([NH:26][S:27]([C:30]1[CH:31]=[N:32][C:33](Cl)=[CH:34][CH:35]=1)(=[O:29])=[O:28])([CH3:25])([CH3:24])[CH3:23].F[B-](F)(F)F.[C:42]([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.[F-:55].[K+]>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:22]([NH:26][S:27]([C:30]1[CH:31]=[N:32][C:33]([C:4]2[N:5]([CH:15]3[CH2:18][CH2:17][CH2:16][CH2:42]3)[C:6]3[C:11]([C:3]=2[C:1]#[N:2])=[CH:10][C:9]([F:55])=[C:8]([CH3:12])[CH:7]=3)=[CH:34][CH:35]=1)(=[O:29])=[O:28])([CH3:25])([CH3:24])[CH3:23]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 3-cyano-1-cyclopentyl-5-fluoro-6-methyl-1H-indol-2-ylboronic acid (125 mg, 0.42 mmol, 90%)[prepared as in Example 6, Step E], N-tert-butyl-6-chloropyridine-3-sulfonamide (69 mg, 0.28 mmol), tri-tert-butylphosphonium tetrafluoroborate (10 mg, 0.034 mmol), Pd2(dba)3 (16 mg, 0.017 mmol) and potassium fluoride (150 mg, 2.58 mmol) in THF (2.0 mL) was stirred at 40° C. overnight. The solvent was then evaporated and the residue purified on silica gel eluting with 0 to 10% ethyl acetate in CH2Cl2 to provide N-tert-butyl-6-(3-cyano-1-cyclopentyl-5-fluoro-6-methyl-1H-indol-2-yl)pyridine-3-sulfonamide (99 mg, 78%).

Workup

customThe solvent was then evaporated
customthe residue purified on silica gel eluting with 0 to 10% ethyl acetate in CH2Cl2

Sources & evidence

ORD record: ord-22d6d98adfbe411a9b0a31b2e7c31825
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735414B2

Reaction notes

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