3-Heptanamine → 5-(3,4-Dichlorophenyl)-3-aminoheptane 4-amino-pyridine

HRID 275692Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6](C2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([Cl:16])C=2)[C:7]=1[NH2:8].[NH2:17][CH:18]([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:19][CH3:20].[CH3:25][CH2:26][C@@H]([C@H](NC([C@@H](NC(CNC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](N)CCC(O)=O)=O)C)=O)CC(C)C)=O)CCC(O)=O)=O)CC(C)C)=O)C)=O)CCCN=C(N)N)=O)=O)C)=O)C(N[C@H](C(N[C@H](C(N[C@H](C(N)=O)C)=O)CCC(N)=O)=O)CC1C=CC=CC=1)=O)C.CC([O-])(C)C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[Cl:16][C:11]1[CH:24]=[C:23]([CH:22]([CH2:25][CH3:26])[CH2:21][CH:18]([NH2:17])[CH2:19][CH3:20])[CH:14]=[CH:13][C:12]=1[Cl:15].[NH2:8][C:7]1[CH:6]=[CH:5][N:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 2 (1 mmol), 3-aminoheptane (1.2 mmol), Pd2(DBA)3 (0.02 mol, 4 mol % Pd, 18 mg), BINP (0.04 mmol, 25 mg), NaOtBu (1.4 mmol, 134 mg), and toluene (0.11 M with 3-bromopyridine, 9 ml) is heated to 70° C. under nitrogen until 2 is consumed. The reaction is then cooled to room temperature, and taken up in 10 ml diethyl ether, washed 3 times with 10 ml saturated brine, dried over MgSO4, and condensed in vacuo . The crude product is purified by flash chromatography to afford 3.

Workup

customis consumed
temperatureThe reaction is then cooled to room temperature
washwashed 3 times with 10 ml saturated brine
dry with materialdried over MgSO4, and condensed in vacuo
customThe crude product is purified by flash chromatography
customto afford 3

Sources & evidence

ORD record: ord-d212d5643d064c1aa8b036da5f204475
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06352990B1

Reaction notes

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