Phosphorus oxychloride → HCID 89719227, compound

HRID 1480756Notes

Reaction equation

[CH2:1]([O:8][CH:9]([C:14]1[CH:15]=[C:16]([CH:36]=[CH:37][CH:38]=1)[CH2:17][C:18]1[N:19]=[C:20](O)[C:21]2[C:29]3[C:24](=[CH:25][C:26]([C:30]([O:32][CH3:33])=[O:31])=[CH:27][CH:28]=3)[NH:23][C:22]=2[N:34]=1)[C:10]([F:13])([F:12])[F:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:41])=O>C([O-])(O)=O.[Na+]>[CH2:1]([O:8][CH:9]([C:14]1[CH:15]=[C:16]([CH:36]=[CH:37][CH:38]=1)[CH2:17][C:18]1[N:19]=[C:20]([Cl:41])[C:21]2[C:29]3[C:24](=[CH:25][C:26]([C:30]([O:32][CH3:33])=[O:31])=[CH:27][CH:28]=3)[NH:23][C:22]=2[N:34]=1)[C:10]([F:13])([F:12])[F:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of methyl 2-(3-(1-(benzyloxy)-2,2,2-trifluoroethyl)benzyl)-4-hydroxy-9H-pyrimido[4,5-b]indole-7-carboxylate (0.395 g, 0.757 mmol) in phosphorus oxychloride (6 mL, 64.4 mmol) was heated to 90° C. for 2 hours then after cooling, it was concentrated to dryness to give 650 mg as a brown foam which was suspended in sat. NaHCO3 (15 mL) and stirred for 1 hour. The solid was filtered, washed with water (3×2 mL) and dried at 40° C. under high vacuum until constant weight to afford methyl 2-(3-(1-(benzyloxy)-2,2,2-trifluoroethyl)benzyl)-4-chloro-9H-pyrimido[4,5-b]indole-7-carboxylate (375 mg, 92% yield) as a tan solid and used as such in the next step: MS m/z 540.2 (M+H)+; HPLC 92%, RT 2.51 minutes.

Workup

temperatureafter cooling
concentrationit was concentrated to dryness
customto give 650 mg as a brown foam which
filtrationThe solid was filtered
washwashed with water (3×2 mL)
customdried at 40° C. under high vacuum until constant weight

Sources & evidence

ORD record: ord-555a883e215d4d6897ebdb0215fee0f3
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409906B2

Reaction notes

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