Sodium Carbonate → HCID 86708149, compound

HRID 1747150Notes

Reaction equation

HRID 1747150 reaction equation
FC(F)(F)S(O[C:7]1[CH2:8][CH2:9][N:10]([C@@H:13]2[CH2:20][C@H:16]3[O:17][CH2:18][CH2:19][C@@:15]3([C:21]([N:23]3[CH2:32][CH2:31][C:30]4[N:29]=[CH:28][C:27]([C:33]([F:36])([F:35])[F:34])=[CH:26][C:25]=4[CH2:24]3)=[O:22])[CH2:14]2)[CH2:11][CH:12]=1)(=O)=O.[C:39]1(B(O)O)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C([O-])([O-])=O.[Na+].[Na+]>C(COC)OC.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:39]1([C:7]2[CH2:8][CH2:9][N:10]([C@@H:13]3[CH2:20][C@H:16]4[O:17][CH2:18][CH2:19][C@@:15]4([C:21]([N:23]4[CH2:32][CH2:31][C:30]5[N:29]=[CH:28][C:27]([C:33]([F:34])([F:36])[F:35])=[CH:26][C:25]=5[CH2:24]4)=[O:22])[CH2:14]3)[CH2:11][CH:12]=2)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 86708150HCID 86708150, compound

Product 1

HCID 86708149HCID 86708149, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of the product of Step B (50 mg, 0.09 mmol, 1 eq), phenylboronic acid (22 mg, 0.18 mmol, 2 eq), (Ph3P)4Pd (10 mg, 0.009 mmol, 0.1 eq) and 2 M Na2CO3 (0.1 mL) in dimethoxyethane (1 mL) under N2 was warmed to 80 C in a screw-top vial overnight. The solution was cooled to rt, and concentrated. Purification by column chromatography (4 g) eluting with 50 to 100% ethyl acetate/heptane afforded the title compound of Step C. Calculated for C28H30F3N3O2: 498.2 (M+1). found: 498.3.

Workup

  1. concentrationconcentrated
  2. customPurification by column chromatography (4 g)
  3. washeluting with 50 to 100% ethyl acetate/heptane

Sources & evidence

ORD record
ord-1a9eaaa9de8747fdb0158f8adf46aa6b
Source dataset
uspto-grants-2015_10
Patent number
US09150532B2

Reaction notes

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