1,2-Dimethoxyethane → HCID 68096602, compound

HRID 1918964Notes

Reaction equation

HRID 1918964 reaction equation
[C:1]([O:4][CH2:5][C:6]1[C:11]([N:12]2[CH2:23][CH2:22][N:21]3[C:14](=[CH:15][C:16]4[CH2:17][C:18]([CH3:25])([CH3:24])[CH2:19][C:20]=43)[C:13]2=[O:26])=[CH:10][CH:9]=[CH:8][C:7]=1Br)(=[O:3])[CH3:2].[CH2:28]([N:30]1[CH2:35][CH2:34][N:33]([C:36]2[CH:37]=[CH:38][C:39]([NH:42][C:43]3[C:44](=[O:59])[N:45]([CH3:58])[CH:46]=[C:47](B4OC(C)(C)C(C)(C)O4)[CH:48]=3)=[N:40][CH:41]=2)[CH2:32][CH2:31]1)[CH3:29].C([O-])([O-])=O.[Na+].[Na+].COCCOC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)Cl>[CH2:28]([N:30]1[CH2:35][CH2:34][N:33]([C:36]2[CH:37]=[CH:38][C:39]([NH:42][C:43]3[C:44](=[O:59])[N:45]([CH3:58])[CH:46]=[C:47]([C:7]4[C:6]([CH2:5][O:4][C:1](=[O:3])[CH3:2])=[C:11]([N:12]5[CH2:23][CH2:22][N:21]6[C:14](=[CH:15][C:16]7[CH2:17][C:18]([CH3:24])([CH3:25])[CH2:19][C:20]=76)[C:13]5=[O:26])[CH:10]=[CH:9][CH:8]=4)[CH:48]=3)=[N:40][CH:41]=2)[CH2:32][CH2:31]1)[CH3:29]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 580439513-(5-(4-Ethylpiperazin-1-yl)pyridin-2-ylamino)-1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-oneHCID 680968852-Bromo-6-[7,7-dimethyl-1-oxo-3,4,7,8-tetrahydro-1H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-2(6H)-yl]benzyl Acetate

Product 1

HCID 68096602HCID 68096602, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a microwave tube equipped with a stirring bar, bromide 167f (150 mg, 0.348 mmol), 190a (306 mg, 0.696 mmol), Pd(PPh3)4 (40.2 mg, 0.0348 mmol), Na2CO3 aqueous solution (1.0 N, 1.15 mL, 1.15 mmol), DME (4 mL) were added. The mixture was reacted in microwave at 130° C. for 10 min. methylene chloride (200 mL) was added and the resulting mixture was washed with water (3×30 mL), brine (30 mL×1), dried over MgSO4, filtered, and removed solvent in vacuo. Silica gel column chromatography (methanol:methylene chloride=5:95) gave 190b.

Workup

  1. customTo a microwave tube equipped with a stirring bar
  2. additionwas added
  3. washthe resulting mixture was washed with water (3×30 mL), brine (30 mL×1)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customremoved solvent in vacuo

Sources & evidence

ORD record
ord-bf09e1a5cd014528b4da3d39b34b61a4
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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