Ethanol → HCID 24758412, compound

HRID 1672398Notes

Reaction equation

HRID 1672398 reaction equation
Br[C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[C:11]3([CH2:15][CH2:14][N:13]([CH:16]4[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]4)[C:12]3=[O:22])[CH2:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.O1CCOCC1.C(O)C.[CH2:34]([NH:36][C:37]([C:39]1[N:44]=[CH:43][C:42](B(O)O)=[CH:41][CH:40]=1)=[O:38])[CH3:35].C(Cl)Cl.C(=O)([O-])[O-].[K+].[K+].O>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:16]1([N:13]2[CH2:14][CH2:15][C:11]3([N:7]([CH2:6][C:5]4[CH:23]=[CH:24][C:2]([C:42]5[CH:41]=[CH:40][C:39]([C:37]([NH:36][CH2:34][CH3:35])=[O:38])=[N:44][CH:43]=5)=[CH:3][CH:4]=4)[CH2:8][CH2:9][CH2:10]3)[C:12]2=[O:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

9

Reactant 7

HCID 702EthanolHCID 962WaterHCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 67355590HCID 67355590, compoundHCID 67356061HCID 67356061, compound

Product 1

HCID 24758412HCID 24758412, compound

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Conditions

Temperature
90 °C

Procedure

To a solution of 1-(4-bromobenzyl)-7-cyclohexyl-1,7-diazaspiro[4.4]nonan-6-one (15 mg, 0.000038 mol; prepared according to procedures analogous to those described for the synthesis of Example 1, steps 1-7) in 1,4-dioxane (1 mL, 0.01 mol) and ethanol (200 μL, 0.003 mol) was added sequentially: {6-[(ethylamino)carbonyl]pyridin-3-yl}boronic acid (15 mg, 0.000077 mol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with DCM (1:1) (3 mg, 0.000004 mol), potassium carbonate (1.0 E1 mg, 0.000077 mol), and water (400 μL, 0.02 mol). The resulting mixture was made in a vial which was then sealed, evacuated, and purged with N2 (g). The mixture was then heated to 90° C. and stirred for 16 h. The crude reaction mixture was then purified by prep. HPLC/MS to afford the desired product. LC/MS: 461.3 (M+1H)+.

Workup

  1. customprepared
  2. customwas then sealed
  3. customevacuated
  4. custompurged with N2 (g)
  5. customThe crude reaction mixture
  6. customwas then purified by prep

Sources & evidence

ORD record
ord-5b6b4ba3821b4c2b94647eeef25cf365
Source dataset
uspto-grants-2011_08
Patent number
US07998959B2

Reaction notes

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