Methanol → HCID 68312674, compound

HRID 1530488Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]1[N:8]([CH:9]=[C:10]([C:16]3[N:20]([CH:21]([CH3:23])[CH3:22])[N:19]=[CH:18][N:17]=3)[N:11]=1)[CH2:7][CH2:6][O:5]2.CC1(C)C2[C:46](=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)[O:45][C:27]2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C[OH:67]>CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:22][CH:21]([N:20]1[C:16]([C:10]2[N:11]=[C:12]3[N:8]([CH:9]=2)[CH2:7][CH2:6][O:5][C:4]2[C:13]3=[CH:14][C:15]([C:27]([O:45][CH3:46])=[O:67])=[CH:2][CH:3]=2)=[N:17][CH:18]=[N:19]1)[CH3:23]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 12-bromo-4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaene (3.00 g, 8.04 mmol), Pd(OAc)2 (0.18 g, 0.81 mmol), Xantphos (930 mg, 1.61 mmol) in MeOH (10.0 mL) and TEA (50.0 mL) was heated at 80° C. under CO (1 atm) overnight. The solid was filtered, the filtrate was concentrated and purified by silica gel chromatography eluting with a 50% gradient of EtOAc in petroleum ether to give methyl 4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaene-13-carboxylate (1.7 g, 61% yield) as a white solid. LCMS (ESI) m/z: 354.2 [M+H+].

Workup

filtrationThe solid was filtered
concentrationthe filtrate was concentrated
custompurified by silica gel chromatography
washeluting with a 50% gradient of EtOAc in petroleum ether

Sources & evidence

ORD record: ord-65ca95f03b2a4c7db23178949ca866a4
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090628B2

Reaction notes

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