Sodium Carbonate → HCID 67960065, compound

HRID 1529379Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][C:6](B(O)O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Br[C:14]1[CH:19]=[N:18][CH:17]=[C:16]([CH:20]2[CH2:22][CH2:21]2)[N:15]=1.C([O-])([O-])=O.[Na+].[Na+]>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.O1CCOCC1>[CH:20]1([C:16]2[N:15]=[C:14]([C:6]3[CH:5]=[C:4]4[C:9](=[CH:8][CH:7]=3)[NH:1][CH:2]=[CH:3]4)[CH:19]=[N:18][CH:17]=2)[CH2:22][CH2:21]1

Participants

Conditions

Temperature: 100 °C

Procedure

A reaction vessel was charged with indole-5-boronic acid (674 mg, 4.19 mmol, Sigma-Aldrich), 2-bromo-6-cyclopropylpyrazine (1.00 g, 5.02 mmol, Combi-Phos Catalysts Inc.) and Pd(PPh3)4 (242 mg, 0.21 mmol). The tube was sealed. Dioxane (14 mL) and 2 M Na2CO3 (aq.) (6.28 mL, 12.56 mmol) were added. The reaction was stirred and heated in at 100° C. for 7 h. After cooling to RT, the organic layer was separated and dried over anhydrous Na2SO4, filtered and concentrated. The crude was purified by silica gel chromatography, eluting with a gradient of 0-40% EtOAc in hexanes, to provide 5-(6-cyclopropylpyrazin-2-yl)-1H-indole (750 mg, 3.19 mmol, 76% yield) as a white solid. MS (ESI, pos. ion) m/z: 236.1 (M+1).

Workup

customThe tube was sealed
temperatureAfter cooling to RT
customthe organic layer was separated
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated
customThe crude was purified by silica gel chromatography
washeluting with a gradient of 0-40% EtOAc in hexanes

Sources & evidence

ORD record: ord-a84444e6990749dda1cf4b608bc52460
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090593B2

Reaction notes

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