Cesium carbonate → HCID 90041584, compound

HRID 522988Notes

Reaction equation

Br[C:2]1[N:3]=[C:4]2[C:10]([C:11]([NH:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:9][N:8]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:5]2=[N:6][CH:7]=1.[CH3:26][C:27]1[CH:31]=[C:30]([NH2:32])[O:29][N:28]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:14]([NH:13][C:11]([C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([NH:32][C:30]3[O:29][N:28]=[C:27]([CH3:26])[CH:31]=3)[N:3]=2)[N:8]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[CH:9]=1)=[O:12])([CH3:17])([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 2-bromo-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (125 mg, 292 mol), 3-methylisoxazol-5-amine (43.0 mg, 439 mol), xantphos (50.8 mg, 87.7 mol), Pd2(dba)3 (26.8 mg, 29.2 mol) and cesium carbonate (191 mg, 585 mol) in dioxane (2 mL) was heated in a microwave at 150° C. for 20 min. The mixture was cooled then filtered through a pad of celite. The filtrate was concentrated in vacuo then purified by chromatography (silica, 20-75% ethyl acetate in hexanes) to give N-tert-butyl-2-(3-methylisoxazol-5-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (33 mg, 74.2 mol, 25.4%) as a yellow solid. (EI/CI) m/z: 455.3 [M+H].

Workup

temperatureThe mixture was cooled
filtrationthen filtered through a pad of celite
concentrationThe filtrate was concentrated in vacuo
customthen purified by chromatography (silica, 20-75% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-290fca5da42143bea555ac48637dfe96
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334278B2

Reaction notes

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