Methyl 3-Amino-6-bromopyrazine-2-carboxylate → HCID 68529012, compound

HRID 736603Notes

Reaction equation

[N:1]1([S:6]([C:9]2[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=2)(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:18][C:19]1[C:20]([C:26]([O:28][CH3:29])=[O:27])=[N:21][C:22](Br)=[CH:23][N:24]=1>COCCOC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:18][C:19]1[C:20]([C:26]([O:28][CH3:29])=[O:27])=[N:21][C:22]([C:12]2[CH:13]=[CH:14][C:9]([S:6]([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)(=[O:8])=[O:7])=[CH:10][CH:11]=2)=[CH:23][N:24]=1

Participants

Conditions

Temperature: 160 °C

Procedure

4-(Pyrrolidin-1-ylsulfonyl)phenylboronic acid (0.33 g, 1.29 mmol), methyl 3-amino-6-bromopyrazine-2-carboxylate (0.25 g, 1.08 mmol; described in: H. Ellingson, J. Amer. Chem. Soc. 1949, 2798), K3PO3 (3 M, 1.1 mL, 3.2 mmol), and Pd(dppf)Cl2 (0.044 g, 54 μmol) were suspended in ethylene glycol dimethyl ether/water (1.5:0.5 mL) and heated in a microwave oven at 160° C. for 10 min. The reaction was repeated 3 times. The combined product mixtures were evaporated with silica gel and the crude product was purified by chromatography on silica gel using a heptane to ethyl acetate gradient to give 0.96 g (82% yield) of the title compound: MS (ES) m/z 363 (M++1).

Workup

customThe combined product mixtures were evaporated with silica gel
customthe crude product was purified by chromatography on silica gel using a heptane to ethyl acetate gradient

Sources & evidence

ORD record: ord-619a809a2275423a84294bc8a7b6fc77
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595319B2

Reaction notes

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