Water → HCID 51355041, compound

HRID 2385650Notes

Reaction equation

HRID 2385650 reaction equation
Br[C:2]1[CH:24]=[CH:23][C:5]2[C:6]3[N:7]=[C:8]([C:14]([N:16]4[CH2:20][CH2:19][CH2:18][C@@H:17]4[CH2:21][OH:22])=[O:15])[S:9][C:10]=3[CH2:11][CH2:12][O:13][C:4]=2[CH:3]=1.CC1(C)C(C)(C)OB([C:33]2[CH:34]=[N:35][NH:36][CH:37]=2)O1.C(=O)(O)[O-].[Na+].O.C(#N)C>C(OCC)(=O)C.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>[OH:22][CH2:21][C@H:17]1[CH2:18][CH2:19][CH2:20][N:16]1[C:14]([C:8]1[S:9][C:10]2[CH2:11][CH2:12][O:13][C:4]3[CH:3]=[C:2]([C:33]4[CH:34]=[N:35][NH:36][CH:37]=4)[CH:24]=[CH:23][C:5]=3[C:6]=2[N:7]=1)=[O:15]

Participants

8

Reactant 5

HCID 962WaterHCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 67050557HCID 67050557, compound

Product 1

HCID 51355041HCID 51355041, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(8-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-2-yl)-((R)-2-hydroxymethyl-pyrrolidin-1-yl)-methanone (0.297 g, 0.726 mmol), 4,4,5,5-Tetramethyl-2-(1H-pyrazol-4-yl)-1,3,2-dioxaborolane (0.211 g, 1.09 mmol), 2 M Sodium bicarbonate in water (1 mL, 2.0 mmol) and acetonitrile (2 mL, 40 mmol) were combined in a microwave vial and thoroughly purged with nitrogen. Added Tetrakis(triphenylphosphine)palladium(0) (0.0838 g, 0.0726 mmol) and heated on the Emrys microwave at 150° C. for 10 minutes. Cooled to room temperature, diluted with ethyl acetate, washed with brine and concentrated the organic layer in vacuo. Purified by HPLC to give 101 (48 mg, 17% yield, M+1 397.1)

Workup

  1. customthoroughly purged with nitrogen
  2. washwashed with brine
  3. concentrationconcentrated the organic layer in vacuo
  4. customPurified by HPLC

Sources & evidence

ORD record
ord-51df4168614e4851861856b2172cb6f6
Source dataset
uspto-grants-2012_09
Patent number
US08263633B2

Reaction notes

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