Ethanol → HCID 24759310, compound

HRID 1672391Notes

Reaction equation

C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:31]=[CH:30][C:11]([CH2:12][N:13]2[C:17]3([CH2:21][CH2:20][N:19]([CH:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)[C:18]3=[O:28])[CH2:16][C@@H:15]([OH:29])[CH2:14]2)=[CH:10][CH:9]=1.[N:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1.C1(C)C=CC=CC=1.C(O)C>O.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>[CH:22]1([N:19]2[CH2:20][CH2:21][C:17]3([N:13]([CH2:12][C:11]4[CH:30]=[CH:31][C:8]([C:35]5[CH:36]=[CH:37][N:32]=[CH:33][CH:34]=5)=[CH:9][CH:10]=4)[CH2:14][C@H:15]([OH:29])[CH2:16]3)[C:18]2=[O:28])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

Conditions

Temperature: 120 °C

Procedure

A solution of sodium carbonate (10.0 mg, 0.0000943 mol) in water (0.1 mL) was added to a mixture of (3R)-1-(4-bromobenzyl)-7-cyclohexyl-3-hydroxy-1,7-diazaspiro[4.4]nonan-6-one (19.0 mg, 0.0000466 mol; prepared as Example 37), 4-pyridinylboronic acid (8.60 mg, 0.0000700 mol) and tetrakis(triphenylphosphine)palladium(0) (1.6 mg, 0.0000014 mol) in toluene (200 μL, 0.002 mol) and ethanol (100 μL, 0.002 mol). After stirring the mixture at 120° C. for 6 h, the inorganics were separated by filtration and the filtrate was diluted with methanol and adjusted to a pH of ˜2.0 with TFA. The crude product was purified by prep. HPLC to afford the desired product. LC/MS 406.2 (M+1H)+.

Workup

customthe inorganics were separated by filtration
additionthe filtrate was diluted with methanol
customThe crude product was purified by prep

Sources & evidence

ORD record: ord-b810dbe4c0be44d5aaee814d710df550
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998959B2

Reaction notes

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