Thiophenol → HCID 68095272, compound

HRID 1502320Notes

Reaction equation

Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([NH:12][C:13]([CH:15]3[CH2:17][CH2:16]3)=[O:14])[N:8]=[CH:9]2)=[CH:4][CH:3]=1.[C:18]1([SH:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CC(C)([O-])C.[Na+]>O1CCOCC1.CO.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:18]1([S:24][C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[C:7]([NH:12][C:13]([CH:15]4[CH2:17][CH2:16]4)=[O:14])[N:8]=[CH:9]3)=[CH:4][CH:3]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of N-(7-bromoisoquinolin-3-yl)cyclopropanecarboxamide (145 mg, 0.5 mmol), benzenethiol (55 mg, 0.50 mmol), 1,1′-bis(diphenylphosphino)ferrocene (41.8 mg, 0.10 mmol), palladium(II) acetate (22.4 mg, 0.10 mmol) and sodium tert-butoxide (96 mg, 1.0 mmol) in dioxane (15 mL) were stirred at 100° C. overnight under nitrogen. The mixture was diluted with methanol and filtered through a pad of Celite. The pad was washed with methanol. The combined filtrates were concentrated to dryness and purify by Prep-HPLC to give the product (42.5 mg, 26%). LCMS (ESI): RT (Min)=1.202, M+H+=320.9, method=A. 1H NMR (400 MHz, DMSO-d6) δ 10.93 (s, 1H), 9.06 (s, 1H), 8.41 (s, 1H), 8.02 (t, J=0.8 Hz, 1H), 7.84 (d, J=8.8 Hz, 1H), 7.53 (dd, J=1.6, 8.4 Hz, 1H), 7.38-7.31 (m, 5H), 2.09-1.99 (m, 1H), 0.83-0.79 (m, 4H).

Workup

filtrationfiltered through a pad of Celite
washThe pad was washed with methanol
concentrationThe combined filtrates were concentrated to dryness
custompurify by Prep-HPLC

Sources & evidence

ORD record: ord-3c6530e94dfa44b9b902d7b506cc87d6
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206175B2

Reaction notes

Loading…