Ethanol → HCID 59852968, compound

HRID 1670260Notes

Reaction equation

HRID 1670260 reaction equation
[F:1][C:2]1[CH:28]=[C:27]([N+:29]([O-])=O)[CH:26]=[CH:25][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[C:11]#[C:12][CH2:13][N:14]1[CH2:18][C@@H:17]([N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[C@H:16]([OH:24])[CH2:15]1.CN(C=O)C.CCO>[Fe].O>[NH2:29][C:27]1[CH:26]=[CH:25][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[CH:7][C:6]=2[C:11]#[C:12][CH2:13][N:14]2[CH2:18][C@@H:17]([N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[C@H:16]([OH:24])[CH2:15]2)=[C:2]([F:1])[CH:28]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 6228DimethylformamideHCID 59853082HCID 59853082, compound

Product 1

HCID 59852968HCID 59852968, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (3R,4R)-1-(3-(4-(2-fluoro-4-nitrophenoxy)pyridin-3-yl)prop-2-ynyl)-4-(pyrrolidin-1-yl)pyrrolidin-3-ol (35 mg, 0.082 mmol), DMF (1 mL), EtOH (1 mL) and H2O (1 mL) was treated with Fe powder (67 mg, 1.2 mmol, 2.4 mmol) and heated at 100° C. for 45 min. The mixture was filtered through Celite®, made basic with NaHCO3 and concentrate in vacuo. The residue was partitioned between EtOAc and saturated aq. NaHCO3 solution. The EtOAc phase was dried (MgSO4) and concentrated in vacuo to give the crude aniline (16 mg, 50%) which was used directly in the next step without further purification. MS (ESI+): m/z 397.28 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. concentrationconcentrate in vacuo
  3. customThe residue was partitioned between EtOAc and saturated aq. NaHCO3 solution
  4. dry with materialThe EtOAc phase was dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a57577b5f1b64b7e965cd633f4eb59b5
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

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