Water → 10-chloro-5,6-dimethyl-5H-pyrido[3',4':4,5]pyrrolo[2,3-g]isoquinoline

HRID 1668839Notes

Reaction equation

[H-].[Na+].[Cl:3][C:4]1[C:13]2[C:8](=[C:9]([CH3:21])[C:10]3[NH:16][C:15]4[CH:17]=[CH:18][N:19]=[CH:20][C:14]=4[C:11]=3[CH:12]=2)[CH:7]=[CH:6][N:5]=1.[CH3:22]I.O>CN(C)C(=O)C.CCO.CCN(CC)CC.C(Cl)Cl>[Cl:3][C:4]1[C:13]2[C:8](=[C:9]([CH3:21])[C:10]3[N:16]([CH3:22])[C:15]4[CH:17]=[CH:18][N:19]=[CH:20][C:14]=4[C:11]=3[CH:12]=2)[CH:7]=[CH:6][N:5]=1

Participants

Conditions

Temperature: -10 °C

Procedure

50% NaH (90 mg) is added to the solution of 10-chloro-6-methyl-5H-pyrido[3′,4′:4,5]pyrrolo[2,3-g]isoquinoline (400 mg; product known, already published) in N,N-dimethylacetamide (20 ml) cooled to −10° C. The mixture is stirred for 30 min then CH3I (0.11 ml) is introduced and the mixture is stirred again at −10° C. for 2.5 h. Water and CH2Cl2 are added and the organic phase is separated, dried (MgSO4) and dry evaporated. The residue obtained is chromatographed on a silica column by eluting successively with CH2Cl2-EtOH (9:1 v/v) then EtOH-NEt3 (95:5 v/v) to yield respectively 10-chloro-5,6-dimethyl-5H-pyrido[3′,4′:4,5]pyrrolo[2,3-g]isoquinoline (66 mg, 16% yield) and the expected 10-chloro-2,6-dimethyl-2H-pyrido[3′,4′:4,5]pyrrolo[2,3-g]isoquinoline (138 mg, 32% yield) in the form of yellow microcrystals (point melting>260° C.). NMR in agreement.

Workup

stirringthe mixture is stirred again at −10° C. for 2.5 h
customthe organic phase is separated
dry with materialdried (MgSO4)
customdry
customevaporated
customThe residue obtained
customis chromatographed on a silica column
washby eluting successively with CH2Cl2-EtOH (9:1 v/v)

Sources & evidence

ORD record: ord-8a36db42634a48a990f5ae2f0a1496bb
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989467B2

Reaction notes

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