1,2-Dimethoxyethane → HCID 67196905, compound

HRID 544887Notes

Reaction equation

HRID 544887 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH:34]=[O:35])=[CH:5][N:6]2[C@@H:11]1[O:28][C@H:27]([CH2:29][O:30][C:31](=[O:33])[CH3:32])[C@@H:22]([O:23][C:24](=[O:26])[CH3:25])[C@H:17]([O:18][C:19](=[O:21])[CH3:20])[C@H:12]1[O:13][C:14](=[O:16])[CH3:15].[F:36][CH:37]([F:48])[O:38][C:39]1[CH:44]=[CH:43][C:42](B(O)O)=[CH:41][CH:40]=1.COCCOC>O.C/C(/O)=C/C(C)=O.[C-]#[O+].[C-]#[O+].[Rh].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]>[F:36][CH:37]([F:48])[O:38][C:39]1[CH:44]=[CH:43][C:42]([CH:34]([C:4]2[C:3]3[C:7](=[CH:8][CH:9]=[CH:10][C:2]=3[F:1])[N:6]([C@@H:11]3[O:28][C@H:27]([CH2:29][O:30][C:31](=[O:33])[CH3:32])[C@@H:22]([O:23][C:24](=[O:26])[CH3:25])[C@H:17]([O:18][C:19](=[O:21])[CH3:20])[C@H:12]3[O:13][C:14](=[O:16])[CH3:15])[CH:5]=2)[OH:35])=[CH:41][CH:40]=1

Participants

7

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 230821464-(Difluoromethoxy)benzeneboronic acidHCID 715002594-fluoro-1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)indole-3-carboxaldehyde

Product 1

HCID 67196905HCID 67196905, compound

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 5377512Rhodium, dicarbonyl(2,4-pentanedionato)-CatalystHCID 962WaterSolvent2×

Procedure

A mixture solution of 4-fluoro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indole-3-carboxaldehyde (350 mg) obtained in Example 25-(1), 4-(difluoromethoxy)benzeneboronic acid (399 mg), (acetylacetonato)dicarbonylrhodium(I) (37 mg) and 1,1′-bis-(diphenylphosphino)ferrocene (79 mg) in H2O (3.6 ml)-1,2-dimethoxyethane (3.6 ml) was stirred at 80° C. under argon atmosphere for 18 hours. The reaction mixture was cooled to room temperature, and thereto was added water (10 ml). The mixture was extracted with ethyl acetate (20 ml) 3 times, and the combined organic layer was dried over magnesium sulfate followed by being filtered through an aminosilane-treated silica gel pad. The filtrate was evaporated under reduced pressure to give crude 4-(difluoromethoxy)phenyl 4-fluoro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indol-3-yl methanol, which was used in the subsequent step without further purification.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (20 ml) 3 times
  2. dry with materialthe combined organic layer was dried over magnesium sulfate
  3. filtrationby being filtered through an aminosilane-
  4. additiontreated silica gel pad
  5. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1d79e428b0d74a12bdcb8c1ac27f19f4
Source dataset
uspto-grants-2011_05
Patent number
US07935674B2

Reaction notes

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