N-(tert-Butoxycarbonyl)-1,5-diaminopentane → N-(tert-butoxycarbonyl)-N'-(5-isoquinolyl)-pentamethylenediamine

HRID 10511

Reaction equation

Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.[C:33]([O:37][C:38](=[O:46])[NH:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][NH2:45])([CH3:36])([CH3:35])[CH3:34].CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1>[C:33]([O:37][C:38]([NH:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][NH:45][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2)=[O:46])([CH3:36])([CH3:35])[CH3:34]

Participants

Conditions

Temperature: 70 °C

Procedure

Under nitrogen atmosphere, a suspension of 5-bromoisoquinoline (245 mg), tris(dibenzylideneacetone)palladium(0) (56 mg), 2-(di-tert-butylphosphino)biphenyl (69 mg), N-(5-aminopentyl)carbamic acid tert-butyl ester (282 mg, Tokyo Kasei Kogyo) and sodium tert-butoxide (160 mg) in toluene was stirred with heating at 70° C. for 4.5 hours. The reaction mixture was cooled to room temperature and purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to obtain the title compound (327 mg).

Workup

temperatureThe reaction mixture was cooled to room temperature
custompurified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record: ord-600f4b91275841b0837efb247cf9997c
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094789B2

Linked notes

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