Lithium Hexamethyldisilazide → HCID 67241769, compound

HRID 1970321Notes

Reaction equation

HRID 1970321 reaction equation
[NH2:1][C:2]1[O:3][CH2:4][C@@:5]2([N:21]=1)[C:18]1[CH:17]=[C:16](Br)[CH:15]=[CH:14][C:13]=1[O:12][C:11]1[C:6]2=[CH:7][C:8]([OH:20])=[CH:9][CH:10]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(N(C)C)=CC=CC=2)CCCCC1.[CH3:50][C:51]1([CH3:57])[O:56][CH2:55][CH2:54][NH:53][CH2:52]1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[NH2:1][C:2]1[O:3][CH2:4][C@@:5]2([N:21]=1)[C:18]1[CH:17]=[C:16]([N:53]3[CH2:54][CH2:55][O:56][C:51]([CH3:57])([CH3:50])[CH2:52]3)[CH:15]=[CH:14][C:13]=1[O:12][C:11]1[C:6]2=[CH:7][C:8]([OH:20])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 2733832Lithium HexamethyldisilazideHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 189596742,2-DimethylmorpholineHCID 58466124HCID 58466124, compound

Product 1

HCID 67241769HCID 67241769, compound

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
110 °C

Procedure

A 2-5 ml microwave vial was charged with (S)-2-amino-2′-bromo-5H-spiro[oxazole-4,9′-xanthen]-7′-ol (300 mg, 0.864 mmol) (104780-26-0), Pd2dba3 (39.6 mg, 0.043 mmol), 2′-(dicyclohexylphosphino)-N,N-dimethylbiphenyl-2-amine (40.8 mg, 0.104 mmol) and 2,2-dimethylmorpholine (299 mg, 2.59 mmol). The mixture was capped with argon and LiHMDS (1M in THF) (4321 μL, 4.32 mmol) was added and the vial was sealed and heated at 110° C. in microwave reactor for 1 hr. The reaction mixture was quenched by addition of 2 ml water and EtOAc, then saturated NH4Cl was added. The organic layer was filtered through Celite, concentrated in vacuo and purified on a 40 g RediSep column using 15-80% DCM/MeOH/NH4OH in DCM to afford (R)-2-amino-2′-(2,2-dimethylmorpholino)-5H-spiro[oxazole-4,9′-xanthen]-7′-ol.

Workup

  1. additionwas added
  2. customthe vial was sealed
  3. customThe reaction mixture was quenched by addition of 2 ml water and EtOAc
  4. additionsaturated NH4Cl was added
  5. filtrationThe organic layer was filtered through Celite
  6. concentrationconcentrated in vacuo
  7. custompurified on a 40 g RediSep column

Sources & evidence

ORD record
ord-72fb91e687184975995ef3faaee2b067
Source dataset
uspto-grants-2013_04
Patent number
US08426447B2

Reaction notes

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