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

HRID 488722Notes

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 mmol, 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-90d7414938da4bd89c28683ef681d248
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06974808B2

Reaction notes

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