1,1'-Carbonyldiimidazole → HCID 68738175, compound

HRID 2261267Notes

Reaction equation

[CH:1]1N=C[N:3]([C:6]([N:8]2C=N[CH:10]=[CH:9]2)=[O:7])[CH:2]=1.[CH3:13][C:14]1[CH:19]=CC(N)=[CH:16][C:15]=1[B:21]1[O:25][C:24]([CH3:27])([CH3:26])[C:23]([CH3:29])([CH3:28])[O:22]1.[CH:30]1(N)CC1>C1COCC1>[CH:9]1([NH:8][C:6]([NH:3][C:2]2[CH:1]=[CH:13][C:14]([CH3:19])=[C:15]([B:21]3[O:22][C:23]([CH3:29])([CH3:28])[C:24]([CH3:26])([CH3:27])[O:25]3)[CH:16]=2)=[O:7])[CH2:10][CH2:30]1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of CDI (254 mg, 1.57 mmol) and 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine (332 mg, 1.42 mmol) under nitrogen was treated with THF (10 mL) and heated to 50° C. for 45 min. The solution was then cooled to RT and treated with cyclopropylamine (113 μl, 1.64 mmol) and again heated to 40° C. for 11 h. The volatiles were then removed in vacuo (rotary evaporator) and the crude solid was purified on the ISCO 40 g column (15-70% EtOAc in hexanes) affording the title compound as a white amorphous solid. MS (ESI, pos.ion) m/z: 317.2 (M+1).

Workup

temperatureThe solution was then cooled to RT
temperatureagain heated to 40° C. for 11 h
customThe volatiles were then removed in vacuo (rotary evaporator)
customthe crude solid was purified on the ISCO 40 g column (15-70% EtOAc in hexanes)

Sources & evidence

ORD record: ord-0134fc12d3134c659869f124ef5bbd6d
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07846944B2

Reaction notes

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