Tetrahydrofuran → HCID 86627419, compound

HRID 1988793Notes

Reaction equation

C1C2[C:10]3=CC4C=CC(C(O)=O)=CC=4[N:9]3[CH2:8]C=CC=2C=CC=1.[Cl:22][C:23]1[C:28]([C:29]([N:31]2[CH2:36][CH2:35]O[CH2:33][CH2:32]2)=[O:30])=[CH:27][CH:26]=[CH:25][N:24]=1.[CH2:37]1COCC1>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>[Cl:22][C:23]1[C:28]([C:29]([N:31]2[CH:36]3[CH2:35][CH2:37][CH:32]2[CH2:33][N:9]([CH3:10])[CH2:8]3)=[O:30])=[CH:27][CH:26]=[CH:25][N:24]=1

Participants

Conditions

Temperature: 160 °C

Procedure

7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid, 13-cyclohexyl-3-methoxy-6-[3-(4-morpholinylcarbonyl)-2-pyridinyl]-, 1,1-dimethylethyl ester. To a solution of 7H-Indolo[2,1-a][2]benzazepine-10-carboxylic acid, 13-cyclohexyl-3-methoxy-6-(tributylstannyl)-, 1,1-dimethylethyl ester (100 mg, 0.136 mmol) dissolved in THF (2 mL) was added 4-[(2-chloropyridin-3-yl)carbonyl]morpholine (47 mg, 0.21 mmol), TEA (0.029 mL), and tetrakis(triphenylphosphine)palladium (16 mg, 0.014 mmol). This mixture was capped under nitrogen and heated in a microwave at 160° C. for 2 hr. The reaction mixture was filtered purified by prep HPLC under the following conditions: Shimadzu prep. HPLC using Discovery VP software: % A=10% acetonitrile, 90% water, 0.1% TFA; % B=90% acetonitrile, 10% water, 0.1% TFA; Initial % B=30; Final % B=100; Gradient=12 min; Runtime=20 min; Flow rate=40 ml/min; Column=Waters Sunfire 30×100 mm S5. This afforded the title compound (38 mg, 44%) as a yellow paste. MS m/z 634 (MH+).

Workup

customThis mixture was capped under nitrogen
filtrationThe reaction mixture was filtered
custompurified by prep HPLC under the following conditions
customGradient=12 min
customRuntime=20 min

Sources & evidence

ORD record: ord-6b4b24cafc644a8eb42f400f50e99802
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642251B2

Reaction notes

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