Potassium Carbonate → HCID 71515786, compound

HRID 574649Notes

Reaction equation

[CH:1]1(B(O)O)[CH2:3][CH2:2]1.[C:7]([N:10]1[CH2:15][CH2:14][C:13]2[N:16]([C@@H:27]3[C:35]4[C:30](=[C:31](Br)[CH:32]=[C:33]([F:36])[CH:34]=4)[CH2:29][C@H:28]3[OH:38])[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=3)[C:22]#[N:23])[C:12]=2[CH2:11]1)(=[O:9])[CH3:8].C([O-])([O-])=O.[K+].[K+]>CC#N.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:7]([N:10]1[CH2:15][CH2:14][C:13]2[N:16]([C@@H:27]3[C:35]4[C:30](=[C:31]([CH:1]5[CH2:3][CH2:2]5)[CH:32]=[C:33]([F:36])[CH:34]=4)[CH2:29][C@H:28]3[OH:38])[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=3)[C:22]#[N:23])[C:12]=2[CH2:11]1)(=[O:9])[CH3:8]

Participants

Conditions

Temperature: 110 °C

Procedure

According to Scheme 14: A mixture of cyclopropylboronic acid (28 mg, 0.33 mmol), 3-[5-acetyl-1-((1R,2R)-4-bromo-6-fluoro-2-hydroxy-indan-1-yl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl]-benzonitrile (11d) (0.05 g, 0.10 mmol), K2CO3 (83 mg, 0.606 mmol) and tetrakis(triphenylphosphine)palladium(0) (17 mg, 0.005, 0.015 mmol) in CH3CN (2 ml) and water (0.75 ml) was stirred at 110° C. for 2 h under microwave irradiation. The mixture was purified by reverse phase HPLC (CH3CN/water gradient with 0.1% trifluoroacetic acid) to give 9 mg of 3-[5-acetyl-1-((1R,2R)-4-cyclopropyl-6-fluoro-2-hydroxy-indan-1-yl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl]-benzonitrile (20a).

Workup

customThe mixture was purified by reverse phase HPLC (CH3CN/water gradient with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record: ord-1aa790f60146411ba48be9572b9f6e04
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034897B2

Reaction notes

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