Dimethylformamide → 5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine

HRID 1924765Notes

Reaction equation

Br[C:2]1[N:7]=[C:6]2[S:8][C:9]([NH2:11])=[N:10][C:5]2=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:20]2[CH:21]=[N:22][NH:23][CH:24]=2)O1.C([O-])([O-])=O.[Na+].[Na+].CN(C=O)C>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.O>[NH:22]1[CH:21]=[C:20]([C:2]2[N:7]=[C:6]3[S:8][C:9]([NH2:11])=[N:10][C:5]3=[CH:4][CH:3]=2)[CH:24]=[N:23]1

Participants

Conditions

Temperature: 150 °C

Procedure

To a microwave vial, 5-bromothiazolo[5,4-b]pyridin-2-amine (1B, 100 mg, 1.0 equivalent), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (5A, 2.0 equivalent), Na2CO3 (4.0 equivalents), DMF (0.15 M) and H2O (0.73 M) were added. While mixture was under N2, Pd(PPh3)4 was added and the mixture was then heated in a microwave for 3 h at 150° C. The crude mixture was filtered, and purified by preparatory LCMS. Intermediate 5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine (5B) was obtained as a white solid. ESI-MS: m/z 218.0 (M+H)+.

Workup

filtrationThe crude mixture was filtered
custompurified by preparatory LCMS

Sources & evidence

ORD record: ord-bca760025d914d05bc9707ee8b66368a
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178555B2

Reaction notes

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