Ethanol → HCID 69545617, compound

HRID 1016464Notes

Reaction equation

HRID 1016464 reaction equation
[C:1]([O:5][C:6](=[O:28])[N:7]([CH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1)[CH2:8][CH2:9][NH:10][C:11]1[N:16]2[N:17]=[C:18]([CH3:21])[C:19](I)=[C:15]2[N:14]=[C:13]([CH3:22])[CH:12]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:29][C:30]1[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][C:31]=1B(O)O.C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.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:1]([O:5][C:6](=[O:28])[N:7]([CH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1)[CH2:8][CH2:9][NH:10][C:11]1[N:16]2[N:17]=[C:18]([CH3:21])[C:19]([C:34]3[CH:33]=[CH:32][CH:31]=[C:30]([Cl:29])[C:35]=3[Cl:36])=[C:15]2[N:14]=[C:13]([CH3:22])[CH:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27346612,3-Dichlorobenzeneboronic acidHCID 69545705HCID 69545705, compound

Product 1

HCID 69545617HCID 69545617, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of cyclopentyl-[2-(3-iodo-2,5-dimethyl-pyrazolo[1,5-a]pyrimidin-7-ylamino)-ethyl]-carbamic acid tert-butyl ester (38 mg, 0.076 mmol) and 2,3-dichlorobenzeneboronic acid in toluene (0.5 mL)/ethanol (0.5 mL)/2 M aqueous sodium carbonate (0.22 mL) was degassed (3×) by alternately pulling a vacuum followed by repressurization with nitrogen. Tetrakis(triphenylphosphine)palladium (10 mg, 0.009 mmol) was added, and the mixture was degassed (3×) again. The mixture was stirred for 2.5 hours at 100° C., concentrated under reduced pressure, and then chromatographed (4:1 hexanes/ethyl acetate) to give the product as colorless oil (24 mg, 60%): +APcI MS (M+1)+ 518; 1H NMR (CDCl3) δ7.42 (dd, 1 H), 7.30 (dd, 1H), 7.22 (t, 1H), 5.84 (s, 1H ), 4.25-4.10 (br s, 1H), 3.49 (s, 4H), 2.44 (s, 3H), 2.32 (s, 3H), 1.52 (s, 9H).

Workup

  1. customwas degassed (3×)
  2. customthe mixture was degassed (3×) again
  3. concentrationconcentrated under reduced pressure
  4. customchromatographed (4:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-6a9f84a68bea43d3abc73c033e6d3e2c
Source dataset
uspto-grants-2002_11
Patent number
US06476038B1

Reaction notes

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