Sodium Bicarbonate → HCID 89782871, compound

HRID 58099Notes

Reaction equation

Br[C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.[F:15][C:16]1[C:24]2[C:19](=[N:20][CH:21]=[C:22](B(O)O)[CH:23]=2)[NH:18][CH:17]=1.[C:28]([O-:31])(O)=[O:29].[Na+]>O1CCOCC1>[C:28]([OH:31])([C:11]([F:14])([F:13])[F:12])=[O:29].[F:15][C:16]1[C:24]2[C:19](=[N:20][CH:21]=[C:22]([C:2]3[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]4[C:3]=3[CH:4]=[N:5][NH:6]4)[CH:23]=2)[NH:18][CH:17]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A 20 mL microwave vial was charged with a mixture of 4-bromo-6-(trifluoromethyl)-1H-indazole (60 mg, 0.226 mmol), (3-fluoro-1H-pyrrolo[2,3-b]pyridin-5-yl)boronic acid (61.1 mg, 0.340 mmol) and PdCl2(dppf)CH2Cl2 (9.31 mg, 0.011 mmol) in dioxane (4 mL) and aqueous saturated NaHCO3 (2 mL). The resulting brown suspension was heated at 130° C. for 30 minutes in microwave reactor. The reaction mixture was subsequently purified by preparative HPLC, eluting with a gradient of 65-80% acetonitrile (containing 0.035% TFA) in H2O (containing 0.05% TFA). The product fractions were collected and dried to give a TFA salt of the title compound as a dark purple solid (13.1 mg, 18.1%). 1H NMR (400 MHz, CD3OD) δ ppm 7.34 (d, J=2.27 Hz, 1H), 7.50 (d, J=1.01 Hz, 1H), 7.92 (s, 1H), 8.29 (d, J=1.01 Hz, 1H), 8.36 (d, J=2.02 Hz, 1H), 8.62 (d, J=2.02 Hz, 1H); ESI-MS m/z [M+H]+ calc'd for C15H8F4N4, 321.1. found 321.2.

Workup

customThe reaction mixture was subsequently purified by preparative HPLC
washeluting with a gradient of 65-80% acetonitrile (containing 0.035% TFA) in H2O (containing 0.05% TFA)
customThe product fractions were collected
customdried

Sources & evidence

ORD record: ord-111e3dda7108497cb48304c5208dc40f
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434743B2

Reaction notes

Loading…