Dichloromethane → HCID 22480288, compound

HRID 1353767Notes

Reaction equation

HRID 1353767 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[N:12]=[N:13][N:14]([C:16]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[N:15]=3)[CH:9]=2)[N:4]([CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][O:36]2)[N:3]=1.[NH2:41][C:42]1[CH:43]=[C:44](B(O)O)[CH:45]=[CH:46][CH:47]=1.ClCCl.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C(OCC)(=O)C>[O:36]1[CH2:37][CH2:38][CH2:39][CH2:40][CH:35]1[N:4]1[C:5]2[C:10](=[CH:9][C:8]([C:11]3[N:12]=[N:13][N:14]([C:16]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[N:15]=3)=[CH:7][CH:6]=2)[C:2]([C:46]2[CH:47]=[C:42]([NH2:41])[CH:43]=[CH:44][CH:45]=2)=[N:3]1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 922693-Aminophenylboronic acidHCID 22479975HCID 22479975, compound

Product 1

HCID 22480288HCID 22480288, compound

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared according to the procedure described in example 209A using 2-{3-bromo-5-[2-(triphenylmethyl)(1,2,3,4-tetrazol-5-yl)]-1H-indazolyl}perhydro-2H-pyran (0.754 g, 1.27 mmol) in ethylene glycol dimethyl ether (12 mL), 3-aminophenyl boronic acid (0.296 g, 1.91 mmol), [1,1′-bis(diphenylphosphino)ferrocene] complex with dichloromethane (1:1) (0.147 g, 0.127 mmol), and potassium phosphate (1.35 g, 6.35 mmol). It was isolated after chromatographic purification using 25% ethyl acetate in hexanes (0.246 g, 32% yield): ES-MS (m/z) 604 [M+H]+.

Workup

  1. customIt was isolated
  2. customafter chromatographic purification

Sources & evidence

ORD record
ord-733ebd358596480dab9d187a77c2a6b4
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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