Potassium Carbonate → HCID 67233815, compound

HRID 1465964Notes

Reaction equation

[CH2:1]([O:5][C:6]([C:8]1[C:9]([OH:18])=[C:10]2[CH:17]=[CH:16][S:15][C:11]2=[C:12](Br)[N:13]=1)=[O:7])[CH2:2][CH2:3][CH3:4].[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCOCC1>[CH2:1]([O:5][C:6]([C:8]1[C:9]([OH:18])=[C:10]2[CH:17]=[CH:16][S:15][C:11]2=[C:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:13]=1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 7-bromo-4-hydroxy-thieno[2,3-c]pyridine-5-carboxylic acid butyl ester (example 43a, 165 mg, 0.5 mmol), phenylboronic acid (94 mg, 0.75 mmol), tetrakis(triphenylphosphine) palladium(0) (59 mg, 0.05 mmol), potassium carbonate (208 mg, 1.5 mmol), and anhydrous 1,4-dioxane (3 ml) was heated in a microwave oven at 140° C. for 15 min. Then silica gel was added and the mixture concentrated in vacuo. The residue was added on top of a short column filled with silica gel. Elution with ethyl acetate:hexanes=9:1 and in vacuo concentration gave the title compound as a yellowish oil (95 mg); MS-(+)-ion: MS-(+)-ion: M+1=328.0.

Workup

additionThen silica gel was added
concentrationthe mixture concentrated in vacuo
additionThe residue was added on top of a short column
additionfilled with silica gel
washElution with ethyl acetate
concentrationhexanes=9:1 and in vacuo concentration

Sources & evidence

ORD record: ord-4afd5616bbfc43a5b9faae6251eae29f
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000006B2

Reaction notes

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